A Fleet
Per the A/B Fleet rules, the following skippers have qualified for the A Fleet:
| Skipper | Qualifying Event | Expires |
| Bill Menninger | 2008 Fleet Champion | Perpetual |
| Terry Gloege | 1997, 2000, 2003, & 2007 Fleet Champion | Perpetual |
| Mark Gaudio | 2004, 2005, & 2006 Fleet Champion | Perpetual |
| Bob Yates | 2002 Fleet Champion | Perpetual |
| Phil Ramser | 2001 Fleet Champion | Perpetual |
| Bob Emmet | 1999 Fleet Champion | Perpetual |
| Tom Schock | 1998 Fleet Champion | Perpetual |
| John Fuller | Sunkist Series #1/CHOC Regatta | 11/1/09 |
| Jim Kerrigan | Sunkist Series #1/CHOC Regatta | 11/1/09 |
| Lee Sutherland | Class/Fleet 1 Championships | 10/5/09 |
| Carter Ford | Tune-Up Regatta | 9/27/09 |
| Peter Haynes | Earl Corkett Regatta & Leukemia Cup | 5/18/09 |
| George Twist | Fleet 1 Board Meeting | 3/20/09 |
| Tom Corkett | W.D. Schock Memorial Regatta | 3/2/09 |
| Chris Allen | 2007 Results | 1/1/09 |
| Tucker Cheadle | 2007 Results | 1/1/09 |
| Steve Schupak | 2007 Results | 1/1/09 |
The following B Fleet skippers have won one high point event (are half way to qualifying for the A Fleet):
| Skipper | Qualifying Event | Expires |
| Richard Blatterman | Sunkist Series #1/CHOC Regatta | 11/1/09 |
| Ross Watanabe | Class/Fleet 1 Championships | 10/5/09 |
| Ted Munroe | Tune-Up Regatta | 9/27/09 |
| Jeff Gordon | Lorin Weiss Memorial | 3/22/09 |