7 of the Greatest Heads-Up Battles in Poker History

By Geoff Fisk
August 22, 2018

Poker fans were treated to a pair of amazing heads-up matches at the end of the 2018 WSOP, with both the Main Event and the Big One for One Drop ending with one-on-one battles for the ages. That got me thinking about the fact that there have been some amazing heads-up battles we’ve been privileged to bear witness to since the advent of televised poker. With that in mind, let’s take a look at seven of the greatest heads-up battles in poker history.

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.

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.

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.

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.



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Geoff Fisk poker author
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Geoff Fisk

Geoff Fisk’s infatuation with poker began as he watched Chris Moneymaker go on his legendary run to win the 2003 World Series of Poker Main Event. Geoff took his first shot at online poker in 2006 and continued to grind it out on the virtual tables for the better part of a decade, before taking […]


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