Top Ten Greatest Heads-Up Grudge Matches

5. The bankroll verification fail

One of the craziest heads-up matches in online poker history happened completely by accident.

The very appropriately named "Whoopsy_Dazy" was being staked and as part of his deal, was required to occasionally prove his bankroll to his backers by sitting at a high stakes table.

Unfortunately for this player he had self-excluded from cash games, which meant that the moderator tasked with confirming his bankroll amount suggested he sit down at a $5,000 heads-up Sit and Go, saying the odds of it filling were very unlikely.

Would you believe it, it did fill. This left Whoopsy_Dazy having to play the match and he lost his entire $5,000 roll.

4. The durrrr challenge

Tom Dwan

This is the second appearance in this list for Tom Dwan and arguably the challenge that made his name, even though it is yet to finish.

In 2009, Dwan issued a challenge to "anyone but Phil Galfond" that he could beat them over 50,000 hands at heads-up No-Limit and/or Omaha at stakes of $200/$400 or higher.

He even gave them great odds - if he won he got $500,000, if they won he gave them $1,500,000.

This caused a buzz in the poker community with speculation over who would face Dwan first. Eventually, the first challenger was unveiled as Patrik Antonius and Daniel 'junglemandan' Cates emerged as the second challenger.

Sadly Black Friday put them both on hold and we still haven't seen the full 50,000 hands played out on either challenge. To date, 19,335 hands have been played against Cates, with Dwan down $1,251,059; 39,436 hands have been played with Antonius, this time with Dwan up $2,059,719.50.

3. Isildur vs Ivey/Dwan/Antonius

The enigma

Before we knew who he was, Viktor "Isildur1" Blom was one of the biggest enigmas the game had ever seen - an unknown Swedish player who was winning and losing seven-figure sums against the best players in the world.

One of the most exciting moments ever seen during this mystery period in 2009 saw him nine-tabling $500/$1,000 heads-up No-Limit against Tom Dwan, Phil Ivey, and Patrik Antonius at the same time.

I'll say that again: nine-tabling $500/$1,000 heads-up No-Limit against Tom Dwan, Phil Ivey, and Patrik Antonius at the same time on Full Tilt.

Heads-up is a hard game to multitable, $500/$1,000  No-Limit is the highest limit ever played  online, and Dwan, Ivey, and Antonius were considered by many to be the best three heads-up players in the world.

What Blom was doing at that moment was arguably about the toughest thing you could do in poker, but amazingly you know he would have played more tables if he had the chance.

2. Mike McDermott vs Teddy KGB

Alright, this one may have been fictional but it is such an infamous heads-up match that it needs mentioning.

The cult poker movie Rounders opens and closes with a 'heads-up for rolls' battle between Matt Damon's Mike McDermott and underground poker club boss 'Teddy KGB', played by John Malkovich.

The movie begins with McDermott going broke to KGB, but is ultimately redeemed when he defeats him at the end of the movie (with an assist going to an Oreo cookie) leaving him to travel to the World Series of Poker with his winnings. It is one of few Hollywood depictions of a heads-up match in poker and one which played a big role in the popularity of the game in the last 14 years.

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1. Andy Beal vs the Corporation

Andy Beal

From something straight out of a Hollywood movie to something that sounds too audacious for even Hollywood. But this really happened.

American billionaire businessman Andy Beal famously challenged a team of poker players known as 'The Corporation' in a series of high stakes heads-up Limit Hold 'em matches in Las Vegas between 2001 and 2006.

The Corporation really was a Who's Who of poker and included Doyle Brunson, Phil Ivey, Jennifer Harman, Howard Lederer, Gus Hansen, Ted Forrest, Chip Reese and Barry Greenstein.

Beal employed a number of methods to take the pros out of their comfort zone including continually raising the stakes as high as $100,000/$200,000, forcing them to play early in the morning and occasionally making random plays prompted by an alarm clock buzzer on his person to avoid becoming predictable or show off tells.

Although Beal was ultimately a loser in the battles overall he did score some major victories, most notably breaking the pros in 2004 and winning $11.7 million in one session. The Corporation had the last laugh, however, as in the final battle Beal lost $16.6 million to Phil Ivey in 2006.

The whole thing is chronicled in the excellent book The Professor, the Banker, and the Suicide King.

The PokerStrategy.com Heads-up Championship

After weeks of planning the PokerStrategy.com Heads-up Championship begins next week, with a total of 14 videos to be produced by 8 PokerStrategy.com coaches including some of the world’s best players.

They will be taking each other on over a series of 90-minute heads-up matches. At the end of 90 minutes, the coach in profit after rake will progress to the next round.

The first match is scheduled to take place on Tuesday, November 27 with the final due to play out on Thursday, December 6.

This week, we will be announcing the players who will participate with a live draw on Sunday, November 25.

For more information on the live draw and how you can watch it, visit our dedicated forum thread:

Forum: The PokerStrategy.com Heads-Up Championships

By Barry Carter l Barry Carter on Twitter