| Time | | | | | | | |
| Sat | 5/16/2009 | 11:30 | SA7-O8 | Perf (fleet) | Performance Series - Race 1 (Olympic) | score | |
| Sat | 5/23/2009 | 11:30 | SA7-S3 | Perf (fleet) | Performance Series - Race 2 (W-L) | score | |
| Sat | 5/30/2009 | 11:30 | SA7-P5 | Perf (fleet) | Performance Series - Race 3 (Trapezoid) | score | |
| Sun | 5/31/2009 | 11:35 | SA7-X2 | Lady (fleet) | Lady Skipper Series - Race 1 | score | |
| Sat | 6/6/2009 | 11:30 | SA7-O1 | Perf (fleet) | Performance Series - Race 4 (Olympic) | score | |
| Sun | 6/7/2009 | 11:30 | SA7-T5 | Casu (fleet) | Casual Series - Race 1 | score | |
| | 11:45 | SA7-T5 | Double (fleet) | Double Handed Challenge | score | |
| Sat | 6/13/2009 | 11:00 | SA7-S2 | Perf (fleet) | Performance Series - Race 5 (W-L) UK-Halsey | score | |
| | 13:05 | SA7-S2 | Perf (fleet) | Performance Series - Race 6 (W-L) UK-Halsey | score | |
| Fri | 6/19/2009 | 20:24 | CHI->MCITY | Long (fleet) | Long Distance Series - Race 1 (Chi to MI City) | score | |
| Sun | 6/21/2009 | 9:00 | MCITY->CHI | Long (fleet) | Long Distance Series - Race 2 (MI City to Chi) | score | |
| Wed | 6/24/2009 | 18:40 | BEER13 | YCC (fleet) | Beer Can - Yacht Club Challenge - Race 1 | score | |
| Sat | 6/27/2009 | 11:30 | SA7-P3 | Perf (fleet) | Performance Series - Race 7 (Trapezoid) | score | |
| Sun | 7/5/2009 | 11:30 | SA7-X3 | Lady (fleet) | Lady Skipper Series - Race 2 | score | |
| Wed | 7/8/2009 | 18:40 | SA7 | YCC (fleet) | Beer Can - Yacht Club Challenge - Race 2 | score | |
| Sat | 7/11/2009 | 10:00 | ZIMMER | Long (fleet) | Long Distance Series (Gene Zimmer) - Race 3 | score | |
| Sun | 7/12/2009 | 11:30 | SA7-S2 | Comp (fleet) | Competition Series - Race 1 (Olympic) | score | |
| Sun | 7/26/2009 | 11:30 | SA7-C7 | Casu (fleet) | Casual Series - Race 2 (Vintage Boat Race) | score | |
| Sun | 8/2/2009 | 11:30 | SA7-P8 | Comp (fleet) | Competition Series - Race 2 (Trapezoid) | score | |
| Wed | 8/5/2009 | 18:40 | SA7 | YCC (fleet) | Beer Can - Yacht Club Challenge - Race 3 | score | |
| Sat | 8/8/2009 | 11:30 | BEER02 | Casu (fleet) | Casual Series - Race 3 | score | |
| | | SA7-P6 | Single (fleet) | Single Handed Challenge | score | |
| Sun | 8/9/2009 | 11:00 | SA7-S6 | Comp (fleet) | Competition Series - Race 3 (W-L) Crowley's | score | |
| | 12:35 | SA7-S6 | Comp (fleet) | Competition Series - Race 4 (W-L) Crowley's | score | |
| Sun | 8/16/2009 | 10:00 | SKIP-CLUB | Long (fleet) | Long Distance Series (Skippers Club) - Race 4 | score | |
| Sun | 8/23/2009 | 11:30 | SA7-X1 | Lady (fleet) | Lady Skipper Series - Race 3 | score | |
| Sat | 8/29/2009 | 11:30 | SA7-P8 | Lady (fleet) | Lady Skipper Series - Race 4 | score | |
| Sun | 8/30/2009 | 11:30 | SA7-O1 | Comp (fleet) | Competition Series - Race 5 (Olympic) | score | |
| Sun | 9/13/2009 | 11:00 | SA7-S1 | Comp (fleet) | Competition Series - Race 6 (W-L Sprint) | score | |
| | | SA7-S2 | Comp (fleet) | Competition Series - Race 7 (W-L Sprint) | score | |
| Sat | 9/19/2009 | 11:00 | SA7-S4 | Comm (fleet) | Commodores Cup - Race 1 | score | |
| | | SA7-W4 | Comm (fleet) | Commodores Cup - Race 2 | score | |
| Sun | 9/20/2009 | 11:00 | SA7-O3 | Comm (fleet) | Commodores Cup - Race 3 | score | |
| Sat | 9/26/2009 | 11:00 | SA7-X7 | Open (fleet) | Goose Island MORF Open - Race 1 | score | |
| | | SA7-Y7 | Open (fleet) | Goose Island MORF Open - Race 2 | score | |
| Sun | 9/27/2009 | 11:00 | SA7-X6 | Open (fleet) | Goose Island MORF Open - Race 3 | score | |
| Wed | 9/30/2009 | 11:30 | SA7 | Boty (fleet) | Boat of the Year | score | |
| | | | Season (fleet) | Season Summary | score | |
