| Event | Dates | Classes |
| SAISA Cressy Qualifiers | 09/13/08 - 09/14/08 | High School Laser, Radial |
| Clearwater Championships | 10/04/08 - 10/05/08 | Optimist, C420, Laser, Radial & 4.7 |
| Clearwater Challenge | 11/01/08 - 11/02/08 | WFPHRF Suncoast BOTY |
| CCSC - Carlise Classic Regatta | 11/15/08 - 11/16/08 | Multi-Class Bay & Gulf Racing |
| Laser Midwinter's East | 02/18/09 - 02/22/09 | Laser, Radial & 4.7 |
| Snipe 71st Midwinter Championship | 03/08/09 - 03/11/09 | Snipe |
| Sunfish Midwinter Championship | 03/19/09 - 03/22/09 | Sunfish |
| Clark Mills Regatta | 04/04/09 - 04/05/09 | Optimist, Laser, Radial & 4.7 |
| Conch Quest Regatta to Key West | 05/11/09 - 05/18/09 | WFPHRF All Regions BOTY |