The $25,500 buy-in High Roller Heads-Up Event, part of the 2008 PokerStars World Championship of Online Poker, kicked off on Sunday afternoon. It attracted one of the most competitive fields ever assembled for an online poker event, including nearly every member of Team PokerStars Pro. The tournament started with 64 players, a perfect field, and will pay out money to the top eight finishers.

The tournament began with 82 registrations. However, in order to have a perfect field in a heads-up tournament, it must have a multiple of 64 players. The final 18 players to register had their money refunded. It was the WCOOP’s first $25,000 buy-in event, marking a new milestone for PokerStars and another statement on the popularity of online poker. The WCOOP also sports two $10,300 buy-in events.

One of the featured pairings early on pitted three-time World Series of Poker bracelet winner Barry Greenstein against Peter “#1Pen” Neff. Greenstein used to work at software giant Symantec before his professional poker career. He won his first WSOP bracelet in a $5,000 buy-in No Limit Deuce to Seven Draw tournament in 2004. The following year, he took down a $1,500 buy-in Pot Limit Omaha event for bracelet number two. He won a Seven Yard Razz tournament this year for $157,000 and his third piece of WSOP hardware. Greenstein has amassed over $2 million in winnings from World Series of Poker tournaments. Neff finished 36th in the 2008 Main Event and also has three World Poker Tour cashes for a total of $124,980.

Two notable members of Team PokerStars Pro were busted in the first round of play. Katja Thater, who took down a $1,500 buy-in Seven Card Razz tournament during the 2007 WSOP, was ousted. Bill Chen, who won a pair of bracelets in 2006, was also sent packing. Some of the early advancers included gunning4you, philivery2694, snake8484, Gavin Griffin, Hold_emNL, Lee Nelson, ElkY. ILuvAntonius, and RunThisTable. Getting through the first round of the Heads-Up tournament is a notable accomplishment given the strength of the field.

Also reaching the second round of the $25,500 High Roller Heads-Up Event was Dario Minieri. He won his first WSOP bracelet this year after tasting victory in a $2,500 buy-in No Limit Hold’em Six-Handed event, besting Seth Fischer heads-up. He’s one of the top Italian players on the circuit today.

Daniel Negreanu, who plays on PokerStars under the name KidPoker, gambled with J-10 suited against theASHMAN103’s pocket nines. The two were all in pre-flop and the board ran out 3-J-A-3-T. Negreanu spiked a ten on the river, which was all he needed for a second round birth.

A person must win six heads-up matches in order to win the $25,000 Heads-Up event. It’s a grind that will likely take most of the day and involves nearly constant play for those whose matches take longer than others. However, with $1.6 million in the prize pool, it will be time well spent.

Also kicking off today is a $1,050 buy-in No Limit Hold’em tournament. It’s a two day event with a $3 million guarantee, tied for the second largest that the 2008 WCOOP offers. The Main Event begins next Sunday and also runs for two days.

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