The 2009 National Heads-Up Championship kicks off with first-round action from the Clubs bracket, as 64 players begin their quest for the $500,000 top prize. At the feature table, two iconic names collide as Daniel Negreanu faces off against 2003 Main Event champion Chris Moneymaker in a marquee matchup. On the outer tables, the action includes Paul Wasicka vs. Nicholas Joy, Jennifer Tilly vs. Phil Ivey, Don Cheadle vs. David Pham, Dario Minieri vs. Mike Matusow, Ted Forrest vs. Orel Hershiser, Doyle Brunson vs. Vanessa Rousso, and Hevad Khan vs. Scotty Nguyen.
| Name | Type | Role | |
|---|---|---|---|
| Craig Hummer | Host | Himself - Commentator | |
| Leeann Tweeden | Host | Herself - Commentator | |
| Oliver 'Ali' Nejad | Host | Himself - Commentator |