Whether playing against a buddy for nothing at a kitchen table or competing in a prestigious major tournament, heads-up poker can present any player with a unique learning experience.

In this article, we’ll take a look at some very basic aspects of heads-up poker that beginning players should be aware of.

We’ll also lay out some rudimentary practice routines and mathematical equations that may assist in forming part of a knowledge-based foundation for poker enthusiasts who are not very familiar with heads-up play.

Before we begin, a quick disclaimer that this article is NOT intended to act as a substitute for poker lessons, poker training, or strategic for-profit play. Rather, it is intended to provide some very basic knowledge and tips that you may need to be aware of before seeking out a poker coach and/or attempting to become a professional player.

Heads-Up Poker and Heads-up Game Rules

Before we specifically get into poker, let’s take a look at heads-up, one-on-one games and how their rules can significantly impact one’s long-term expectation.

Take the 3×3 grid game of Tic Tac Toe, for example.

The rules of the game are very simple, and are constructed in a way in which the very best human players in the world are equally matched against the very best “computer” players.

Once the “best” skill level is achieved by a pair of heads-up opponents, players can only aspire to a perpetual series of tie games.

On the surface, one might not consider the mathematical aspects of such a game (especially when playing for the first time as a child) – yet a mathematical solution DOES exist.

So now you may be wondering to yourself, “How is this relevant to heads-up poker?

Heads-up Poker Rules

Heads-up poker rules are the same in terms of hand strength and betting rounds as they would be for a full ring game of the same variant.

The Small Blind player also has the button in heads-up poker play, while the Big Blind player will be out of position (and correspondingly will act first) in all postflop betting rounds in games like Texas Hold’em and Omaha, as well as draw poker games.

In ante games like Seven Card Stud, a heads-up format will not change betting positions – they will play out just as they would in a 7 Card Stud game with more players.

Heads-up Poker Basic One vs. One Math, Using Simulations

One fun heads-up poker experiment that beginners may learn from is the practice of playing offline versus a pre-programmed “bot” opponent – one that you can play against without the stress of real money competition.

In such a scenario, a first-time poker player may be able to more firmly grasp the concept of “math versus feel” or intuition as it relates to the game itself. By using a pre-programmed opponent, we can also clearly distinguish how a mathematical edge in heads-up poker is formed.

Let’s take the a play money scenario to illustrate a few things about heads-up poker.

BLINDS: 1000/2000

Player 1 (You): 2001 chips
Bot 1: 4000 chips (programmed to go all-in preflop every hand)

Player 1: 3s-2h
Bot 1: ?-?

Preflop Action: Bot 1 raises the action and goes all-in from the button with an unknown hand. There are now 6000 chips in the pot – with the action now on Player 1 who must decide whether to commit a single chip into the pot or fold and relinquish the pot.

In this controlled, non-real money situation, is there any justification at all to make a case for Player 1 to fold? And if there is only a justification (from a poker strategy perspective) for calling, does Player 1 know this by way of feel, intuition, or simply because Player 1 is presented with a scenario in which the math is so skewed that it is obvious a call is the correct play?

Due to Bot 1’s programming, we can assign a range of “any two cards” to Bot 1’s preflop hole card range.

So with a single chip remaining for Player 1 to commit, is there any hand that Player 1 can hold that has worse than a 1-in-6000 chance of eventually winning the pot at showdown?

The answer is no. Even with the worst heads-up poker hand (3-2 offsuit), Player 1 cannot (or perhaps more appropriately, IS not) a 1-in-6000 underdog versus Bot 1’s range. And it’s not even close.

Even if Bot 1 holds the best possible preflop hand in Texas Hold’em (pocket Aces), Player 1’s 3-2 offsuit is only (approximately) a 1-in-8 underdog to win the pot. That’s a far cry from 1-in-6000.

So Player 1 is faced with a mathematical solution that is so far skewed in favor of contributing the single remaining chip for a “call” that even Player 1 can “feel” or “divine” what the correct play is… but it’s still a math problem at the end of the day.

Let’s create another hypothetical play money scenario with our pre-programmed bot that is tasked with going all-in preflop on every hand.

BLINDS: 1/2

Player 1 Chips: 10000
Bot 1 Chips: 10000

Player 1: Qs-9h
Bot 1: ?-?

Bot 1 goes all-in, and Player 1 (from the Big Blind), is faced with a decision to either call with the remaining 9,998 chips or fold.

Since we know that Bot 1 is pre-programmed to go all-in on every hand, we can again assign a hole card range of “any two cards” to Bot 1.

So… Qs-9h is clearly winning against a range of “any two cards.” Q-7 is the “computer hand” that is typically described as the average hole card strength – and Qs-9h is superior to that hand.

Does this mean (from a poker strategy perspective) that Player 1 is going to make the call, knowing that Qs-9h is indeed a winning play against Bot 1’s range? Or is it better for Player 1 to wait (via folding) for a better situation in which the pot odds are more favorable?

Again, a human player may think that he/she feels or “divines” that folding is the correct play in this scenario, but in the end there is a mathematical solution that provides a clear answer.

How Are Pre-Programmed Scenarios Relevant to Actual Heads-up Poker Play?

These pre-programmed practice modes are relevant to illustrate (in a play-money environment) and define very clear-cut mathematical edges to a beginning player.

And subsequently, to demonstrate that these obvious scenarios will be – for lack of a better term – primarily “unavailable” in a competitive heads-up poker environment in which real money incentives exist for both human players to win.

Two poker players with the exact same heads-up ability who are competing against each other one-on-one is a wash. Add any rake into this environment and both players lose – regardless of whether they are the two best/two worst players, or anywhere in between.

Therefore, if you are genuinely interested in playing heads-up poker for a profit, you must overcome the following barriers or satisfy the following prerequisites before doing so:

• Your skill must be superior to that of your opponent’s
• Your edge must then be large enough to overcome the casino, cardroom, or home game’s rake

How Do I Find Inferior Heads-up Poker Players?

Wouldn’t we all like to know?!

For starters, heads-up private games are usually “not a thing” unless there’s a preliminary marketing effort along with a healthy amount of public interest that precedes them.

If you’re playing online poker, then your best bet may be to try out some of the various poker software programs and apps that may give you a better idea of an opponent’s heads-up poker playing ability.

These products may also be able to assist you with identifying and plugging your own leaks in heads-up play (as well as other poker formats).

Poker Heads-up Tips

The number one poker heads-up tip that I can personally think of is… don’t get cheated!

This may be easier said than done in certain scenarios, but is a risk/possibility that all heads-up poker players should remain acutely aware of.

READ MORE: Poker Cheat Sheets

The real money consequences of getting cheated in a heads-up poker game can present odds equally as devastating as the “play money bot” scenarios I’ve mentioned above.

• If an opponent knows one or more of your hole cards, and/or
• If an opponent knows the eventual community card/hole card/door card board runout

… then you’re already defeated, doomed, and the proverbial “fish” at the table regardless of how well you play the game of poker in a fair playing environment.

And while a lot of publicity exists in terms of being wary when playing high-stakes heads-up poker, the same risk of getting cheated can also exist at low-stakes games. As you might hear some poker players say, “it’s all relative.”

So, assuming you’re not getting cheated, the next two tips I can provide are to:

• Gain experience through actually playing heads-up poker
• Join a poker study group and/or get coached specifically on heads-up poker play

Heads-up Hold’em Strategy

If you are a beginning and/or low-skilled heads-up poker player who is playing as a means to improve, experience real-time training, and limit your losses – then you’ll want to play for the lowest stakes possible.

While $0.01/$0.02 online poker heads-up Hold’em games might become a tad boring or tedious, you’re probably better off using the micro stakes poker games to learn as you go (instead of jumping in to higher stakes games that may expose your poker bankroll to a higher “risk of ruin”).

Contrary to popular belief, higher stakes games may not be easier to master than lower stakes games – whether in a live setting or online.

Aside from this, my advice would be to enjoy the experience!

If you’re willing to engage with heads-up poker or heads-up Hold’em strategy in a way in which the journey is personally rewarding, that may represent enough incentive for you to actually improve upon your skills.

Don’t put your poker bankroll under excessive pressure; don’t toss away the experience and knowledge you’re gaining; and don’t get cheated. That’s about it as far as basic heads-up poker strategy tips go!

Starting Your Poker Experience Through Heads-up Play

Loosely speaking, heads-up poker play may be a great place for you to begin your poker journey.

Think of it as being similar to chess… if you start out training with fewer pieces (fewer variables), then perhaps you can learn from and avoid bad strategy habits before they manifest themselves in more complex scenarios.

By definition, you only have one opponent to concern yourself with when playing heads-up poker. Once a game attracts more players, you’ll be faced with more variables to consider.

If you’re in the mood for shot-taking, then there are seasonal live heads-up shootout events that take place during major tournament series, or you can enter an online heads-up tournament and try your luck.

There are also plenty of heads-up poker Sit & Gos online where you can attempt to defeat a random opponent in a mini-tournament that typically concludes in less than 15 minutes. Or try out a Hyper Turbo blind format that will reduce the skill edge enjoyed by a superior opponent.

Enjoy heads-up poker with friends, online, or in a major live tournament and learn from experience about the potential real money edges that can make you a long-term winner at the tables!

Negreanu’s previous challenge against Doug Polk seemed to ignite a new wave of interest in hyped-up heads-up matches. We know of at least two more challenges expected to happen before the end of the year, one of which sets billionaire recreational player Bill Perkins against 21-year-old poker prodigy Landon Tice.

The Galfond Challenge promises Phil Galfond against Dan “Jungleman” Cates at some point as well. These upcoming matches just scratch the surface of what’s possible in poker’s hottest form of content at the moment.

Image credit: capitalbay.news

What other heads-up matches could set the poker world ablaze? Let’s take a look at five heads-up challenges the poker world needs to see:

Fedor Holz vs. Chris Moneymaker

I’d pay money to watch poker icon Chris Moneymaker take on the semi-retired 27-year-old Fedor Holz. What’s not to like about this matchup, pitting the man who started the poker boom against a player who embodies everything about how the poker dream evolved into the 2010s and beyond?

These two players haven’t announced any such plan to engage in a heads-up battle for the ages. The announcement of the Joker’s Gambit charity chess event, which involves poker pros playing chess for charity, did give us this short exchange between the two:

Fuck that. No getting in labs. Play street chess like the rest of us

— Chris Moneymaker (@CMONEYMAKER) March 4, 2021

Moneymaker is ready to take it to the streets for Joker’s Gambit, while Holz is headed to the lab. A heads-up poker match between the two would likely feature that same approach to preparation.

Holz just came off a win in a heads-up match against Wiktor “Limitless” Malinowski. That challenge featured Holz and Malinowski trading needles over Zoom while they battled.

We need the same setup for Moneymaker vs. Holz.

Doug Polk vs. Wiktor “Limitless” Malinowski

Heads-up “supreme leader” Doug Polk isn’t ever shy about evaluating another player’s poker acumen. The Upswing Poker founder wasn’t impressed with Malinowski’s play against Holz, going so far as to say Malinowski played badly on purpose in an effort to get future HUNL action against other high stakes pros:

Is @Iimitless2 actually this bad or is he playing badly on purpose?

— Doug Polk (@DougPolkVids) March 5, 2021

Polk might not have a lot of poker playing left to do in 2021, as he’s indicated his return to the game to engage in the match against Negreanu marked a temporary return to poker.

The High Stakes Feud battle between Polk and Negreanu yielded delayed stream coverage on multiple poker media channels for every chapter of the match. That simultaneous coverage of the same match is something we’ve never really seen before in poker.

Anything Polk does at the table is must-see at this point, and a Polk-Malinowski match seems like a natural progression from each player’s previous heads-up challenge.

Phil Hellmuth vs. Johnnie Vibes

What kind of dynamic would unfold if modern-era cash game vlogger Johnnie “Vibes” Moreno took on 15-time WSOP bracelet winner Phil Hellmuth heads-up? The upcoming Hellmuth-Negreanu High Stakes Duel II match has the poker community talking, and that match is shaping up as perhaps the biggest poker story of 2021.

Moreno contends that the list of players that are willing to battle Hellmuth heads-up is “a mile long,” and includes Johnnie Vibes himself:

It’s tough cause I agree that PH is an all time icon in poker. But in the year 2021, I have my doubts that he works as hard as the professional field. There’s a list of people a mile long that would be willing to play him HU for 25K hands. I’d join that list.

— Johnnie VIBES (@JohnnieVibes) March 6, 2021

Moreno, a straight shooter and one of the more interesting creators in the poker content space these days, would be a fascinating counterpart to Hellmuth in a HUNL match. Let’s get the live Zoom feed going for this one as well.

Joey Ingram vs. The World

Joey Ingram’s hours of commentary on the Polk-Negreanu challenge seem to have inspired in him a newfound passion for heads-up no-limit hold’em. He’s succeeded in taking down a pair of live heads-up tournaments in Las Vegas since the end of High Stakes Feud.

Both the live appearances and the HUNL play are rare for Ingram, whose playing days were heavy on Pot-Limit Omaha before he settled into his current role as one of poker’s most influential content creators.

Ingram isn’t done with his new venture into HUNL:

I need to find some people to play HUNL sessions against at mid stakes to help me see how my game is coming along gotta test myself against someone else besides the bots

Also – looking for a platform to play games on

— Joey Ingram #passion (@Joeingram1) March 7, 2021

Ingram’s call for HUNL opponents prompted Matt Berkey, Benny Glaser, and David Tuchman to accept Ingram’s challenge.

Any of those matches would make for highly entertaining content. The list of potential other opponents for Ingram is amazing to contemplate; how about Ingram vs. Polk or Ingram vs. Hellmuth?

Tom Dwan vs. Gus Hansen

Season 8 of the newly rebooted High Stakes Poker from PokerGO has featured Tom Dwan in every episode, and Dwan has continued his long-running tradition of dominance on the show. Fresh off of that run, the poker world needs to see the inventor of a seminal heads-up match, the “Durrrr Challenge,” return to those heads-up roots.

If we’re thinking of opponents for Dwan in a “Durrr Challenge” revival, why not Gus Hansen? Seeing these two poker boom icons go at it in 2021 could potentially make for the most intriguing heads-up match on this list.

A mythical Dwan vs. Hansen match probably would be low on solver-approved play and high on entertainment value. Let’s get this high-stakes match going in a live format at the PokerGO Studio.

John Cynn vs. Tony Miles, 2018 WSOP Main Event

In arguably the best photo from the 2018 Main Event (big shout out to Joe Giron), Tony Miles raises John Cynn’s hand in victory after a 10-hour heads-up match for poker’s most coveted prize.

John Cynn bested Tony Miles in a 10-hour heads-up battle for the ages to win the 2018 WSOP Main Event. https://t.co/nTwJ08n45k pic.twitter.com/wsi6ZpW3A2

— PokerNews (@PokerNews) July 16, 2018

That photo summed up the final day of the Main Event perfectly, and we’ve really never seen anything else like it in the history of the Main Event. Cynn and Miles went at it tooth and nail for 199 heads-up hands and Cynn finally wrapped up the victory just before 5 a.m. local time. Even though he was clearly disappointed with the second-place finish, Miles displayed his graciousness and class in an image we’ll never forget.

This was the longest heads-up battle ever recorded to end a WSOP Main Event, and it was a win-win situation for live spectators and viewers watching at home on ESPN. It was so easy to root for either of these guys to win, as Cynn and Miles both came across as great people throughout the duration of the final table.

Both players had raucous support from their respective rails, and ESPN was gifted with a truly entertaining and riveting one-on-one match to end the most watched poker event of the year. Cynn and Miles played aggressively and kept us glued to our screens, as the lead changed 11 times before Cynn finally took down the bracelet to end a Main Event heads-up battle for the ages.

Justin Bonomo vs. Fedor Holz, 2018 Big One For One Drop

What more could we have asked for from the highest-stakes poker tournament in the world?

Fedor Holz posted the greatest year of tournament results we had ever seen in 2016, with more than $16 million in cashes and six wins, including first place in the 2016 $111,111 Big One for One Drop High Roller. Justin Bonomo had defied belief with an even more impressive run in 2018, winning the Super High Roller Bowl events in both China and the US, and racking up nearly $15 million in winnings coming into the biggest buy-in WSOP event of the year.

It was only fitting that the One Drop, back to the $1 million entry format for 2018, came down to Holz vs. Bonomo, giving us a chance to see the two phenoms who’ve put up the two best years ever in tournament poker history go head-to-head for the highest of stakes.

The atmosphere surrounding the One Drop final table was intense, and you could feel that intensity increase to an even higher level once it came down to Holz and Bonomo.

These were the two best players in the world at the moment, and even a first-time viewer could see that these guys take their craft very seriously. Holz’s trademark staredowns, and Bonomo’s precise repetition of his timing and body language on each and every bet were fascinating to watch, and the opportunity to see the hole cards with so much on the line gave us a look inside two of the best poker minds of our time, playing at the highest level.

It’s over. And history is made. @JustinBonomo, congratulations on an amazing y̶e̶a̶r̶ seven months. pic.twitter.com/TQVNZN6Kqw

— PokerNews (@PokerNews) July 18, 2018

Bonomo came away with the bracelet, $10 million in prize money, and the No. 1 spot on the all-time tournament money list, with over $42 million in career earnings, almost $25 of that total accrued in 2018 alone. Holz now sits at No. 4 on the all-time list with over $32.5 million in winnings, with his $6 million runner-up prize in this event being his largest cash ever.

Chris Moneymaker vs. Sam Farha, 2003 WSOP Main Event

This is the heads-up match that sparked the poker boom, and has to be at or near the top of any respectable “best heads-up matchups” list!

If the 2003 WSOP Main Event was a fictional movie, Hollywood could not have scripted two characters that were more perfect for the final heads-up battle than Chris Moneymaker and Sam Farha.

Moneymaker had the perfect name and the perfect story, as an unknown amateur from Tennessee who qualified for the $10k Main Event through an $86 PokerStars satellite back when everyone could play online poker in America. Farha was the epitome of the seasoned poker pro, with the look and demeanor of a true high-stakes fixture, and that unforgettable Humphrey Bogart-esque dangling cigarette.

The 2003 Main Event was the first televised WSOP event to feature the hole-card camera, which revolutionized the game and made poker much more enjoyable to watch on television. Poker blew up in popularity due in large part to the 2003 WSOP, with so many viewers living vicariously through Moneymaker as he made his improbable run to the bracelet and $2.5 million prize.

This matchup will always be remembered for the most famous bluff of all time, as Moneymaker goes all in with King-high against Farha’s top pair. Farha correctly guesses that Moneymaker had shoved on a missed flush draw, but after tanking for several minutes he folds anyway.

Moneymaker takes down the tournament on the very next hand, and poker hits the mainstream!

Patrik Antonius vs. Tom Dwan, Durrrr Challenge

The original Durrrr Challenge brings forth memories of the golden age of online poker, when one could log into Full Tilt Poker, sit on the virtual rail, and watch some of the highest-stakes poker games in the world right on their laptop.

Tom “Durrrr” Dwan was one of the most intriguing success stories to come out of this era, starting with a $50 bankroll on Full Tilt and playing his way all the way up to the nosebleed stakes.

In 2009, the then-22-year-old Dwan challenged “anyone but Phil Galfond” to a heads-up match at minimum limits of $200/$400. The matches were intended to be 50,000 hands long, with Dwan receiving an additional $500k from his opponent if he was ahead at the end of the match, but paying his opponent $1.5 million if they were ahead of Dwan after 50k hands.

High-stakes fixture Patrik Antonius was the first to accept the challenge, and between January 2009 and August 2010, the two Full Tilt pros logged 39,436 hands of heads-up No Limit Hold’em and Pot Limit Omaha.

Highlights from the challenge include an insane 15-hour session on June 19, 2009, which featured a $477,555.50 pot won by Antonius. Despite that massive loss, Dwan still came out ahead nearly $750K ahead for the session!

The two players eventually settled the match and the bet, not quite making it to the 50k hands mark, with Durrrr ahead $2,059,719.50.

Andy Beal vs. the Corporation

Sometimes, the most fascinating poker games are the ones we don’t get to see. It’s amazing to contemplate what it would have been like to watch the heads-up matches between Texas billionaire Andy Beal and the “Corporation,” a collection of the world’s best high-stakes poker players.

Reading The Professor, the Banker and the Suicide King, the excellent book by Michael Craig, brings us pretty close to that experience. The book chronicles a series of games, believed to be the highest-stakes games of all time, that took place in Las Vegas in the early 2000s between Beal and a collection of pros that included Ted Forrest, Jennifer Harman, Howard Lederer, Chip Reese, and Doyle Brunson, just to name a few.

Beal became obsessed with poker after trying it for the first time on a trip to Las Vegas, and on subsequent trips he would ask the pros in the high-stakes section of the Bellagio poker room if they would want to play for stakes that eclipsed even the biggest games that had run there. This escalated into matches that saw Beal and his opponent each put $1 million on the table and play at $20,000/$40,000 limits for hours on end.

The billionaire Beal had the bankroll to play these games, and wanted to test himself against the best players in the world. The Corporation was a group of high-stakes pros who pooled their bankrolls together and were equal shareholders to whatever wins or losses took place in these highest of limit games.

They came to an agreement where Beal would play heads-up Limit Hold’em cash games against rotating members of the Corporation, one at a time. Beal proved to be a worthy foe, and after dropping $2 million to Beal in a session, Barry Greenstein warned the rest of the Corporation that the banker was good enough to possibly break them.

The stakes for these games kept rising as Beal made return trips to Las Vegas, culminating in a heads-up freezeout in late 2003 with limits of $50,000-$100,000 and each side putting $10 million on the table! Beal played a rotating lineup of pros for 11 days before finally losing the last of his $10 million to Todd Brunson, giving the pros the victory in what was at the time the highest-stakes poker game ever played.

Beal, however, wasn’t finished taking his shots at poker’s greatest players, returning to Vegas in May 2004 and challenging the Corporation to raise the limits to a staggering $100,000-$200,000. Beal pushed to find stakes that made even the highest stakes pros uncomfortable, and $100k-$200k proved to be that number. Beal won $6 million off the pros during that trip.

Gus Hansen and Phil Ivey had joined the Corporation by then, and even Ivey refused to play Beal at those limits. Beal returned two weeks later and Ivey did play him at $30k-$60k, but it was Todd Brunson and Howard Lederer who rallied to take $15 million off Beal and send the billionaire back to Texas for good.

Or so we thought. Beal returned to Vegas in 2006 to play another series of matches against the Corporation that ended with Ivey beating Beal for $16.6 million in the final match, netting the Corporation $6.5 million in profit.  Nine years later, in 2015, Beal came back to Las Vegas again and lost $5 million in a rematch with Todd Brunson.

Andy Beal playing HU 50K/100K with Todd Brunson in Bobby’s Room. I’m about to lose my mind

— Kyle Loman (@Kloman22) January 24, 2015

Will Beal be back again? If so, can we get it televised?

Ted Forrest vs. Hamid Dastmalchi

Another fascinating heads-up session gets mentioned a couple of times in The Professor, the Banker and the Suicide King, as two of the Corporation’s pros went to battle against each other at the Mirage in a match that only ended when one player couldn’t physically continue.

Ted Forrest played Hamid Dastmalchi, the 1992 WSOP Main Event champion, in a 100-hour “death match” at $600/$1,200 limits. Information about this legendary session is sparse, but author Michael Craig does give us a few details in the book and in a later article for Bluff Magazine.

Both players are known for their ability to play for hours and even days on end, but this particular game really took its toll on Dastmalchi, who had to be taken out of the Mirage on a stretcher. This was quite possibly the result of 50 packs of cigarettes, chain smoked by the Iranian pro during the session.

For you poker trivia buffs out there, Forrest, a six-time WSOP bracelet winner, also came up on another bracelet while playing this match, as Dastmalchi sold Forrest his Main Event bracelet for $1,500 at the table, which Forrest paid for with three $500 chips.

John Juanda vs. Stanislav Alekhin, 2008 WSOP Europe Main Event

John Juanda’s victory in the 2008 WSOP Europe Main Event is quite possibly the most impressive feat of his Hall of Fame career.

The five-time bracelet winner survived a final table that lasted 19 hours and 10 minutes, a marathon stretch of 484 hands. 240 of those hands were played heads-up, as Juanda outlasted Russia’s Stanislav Alekhin in what goes down as the longest final table in WSOP history.

The heads up portion of the final table took seven hours, and from beginning to end the final table began at 1:23 pm and ended with Juanda taking down the bracelet at 10:32 a.m. the next day.

Both players were clearly exhausted in the final stages of the match, with Juanda stating that his secret to enduring the nearly 20-hour session was English breakfast tea, in which he estimates he downed 80 cups.

Is there a legendary heads-up poker battle you feel we missed and should have been included on this list? Let us know in the comments below.