| Time | | | | | | |
| Sat | 05/16/09 | 11:30:00 AM | SA7-O8 | Perf (fleet) | Performance Series - Race 1 (Olympic) | score |
| Sat | 05/23/09 | 11:30:00 AM | SA7-S3 | Perf (fleet) | Performance Series - Race 2 (W-L) | score |
| Sat | 05/30/09 | 11:30:00 AM | SA7-P5 | Perf (fleet) | Performance Series - Race 3 (Trapezoid) | score |
| Sun | 05/31/09 | 11:35:00 AM | SA7-X2 | Lady (fleet) | Lady Skipper Series - Race 1 | score |
| Sat | 06/06/09 | 11:30:00 AM | SA7-O1 | Perf (fleet) | Performance Series - Race 4 (Olympic) | score |
| Sun | 06/07/09 | 11:30:00 AM | SA7-T5 | Casu (fleet) | Casual Series - Race 1 | score |
| | 11:45:00 AM | SA7-T5 | Double (fleet) | Double Handed Challenge | score |
| Sat | 06/13/09 | 11:00:00 AM | SA7-S2 | Perf (fleet) | Performance Series - Race 5 (W-L) UK-Halsey | score |
| | 01:05:00 PM | SA7-S2 | Perf (fleet) | Performance Series - Race 6 (W-L) UK-Halsey | score |
| Fri | 06/19/09 | 08:24:00 PM | CHI->MCITY | Long (fleet) | Long Distance Series - Race 1 (Chi to MI City) | score |
| Sun | 06/21/09 | 09:00:00 AM | MCITY->CHI | Long (fleet) | Long Distance Series - Race 2 (MI City to Chi) | score |
| Wed | 06/24/09 | 06:40:00 PM | BEER13 | YCC (fleet) | Beer Can - Yacht Club Challenge - Race 1 | score |
| Sat | 06/27/09 | 11:30:00 AM | SA7-P3 | Perf (fleet) | Performance Series - Race 7 (Trapezoid) | score |
| Sun | 07/05/09 | 11:30:00 AM | SA7-X3 | Lady (fleet) | Lady Skipper Series - Race 2 | score |
| Wed | 07/08/09 | 06:40:00 PM | SA7 | YCC (fleet) | Beer Can - Yacht Club Challenge - Race 2 | score |
| Sat | 07/11/09 | 10:00:00 AM | ZIMMER | Long (fleet) | Long Distance Series (Gene Zimmer) - Race 3 | score |
| Sun | 07/12/09 | 11:30:00 AM | SA7-S2 | Comp (fleet) | Competition Series - Race 1 (Olympic) | score |
| Sun | 07/26/09 | 11:30:00 AM | SA7-C7 | Casu (fleet) | Casual Series - Race 2 (Vintage Boat Race) | score |
| Sun | 08/02/09 | 11:30:00 AM | SA7-P8 | Comp (fleet) | Competition Series - Race 2 (Trapezoid) | score |
| Wed | 08/05/09 | 06:40:00 PM | SA7 | YCC (fleet) | Beer Can - Yacht Club Challenge - Race 3 | score |
| Sat | 08/08/09 | 11:30:00 AM | BEER02 | Casu (fleet) | Casual Series - Race 3 | score |
| | | SA7-P6 | Single (fleet) | Single Handed Challenge | score |
| Sun | 08/09/09 | 11:00:00 AM | SA7-S6 | Comp (fleet) | Competition Series - Race 3 (W-L) Crowley's | score |
| | 12:35:00 PM | SA7-S6 | Comp (fleet) | Competition Series - Race 4 (W-L) Crowley's | score |
| Sun | 08/16/09 | 10:00:00 AM | SKIP-CLUB | Long (fleet) | Long Distance Series (Skippers Club) - Race 4 | score |
| Sun | 08/23/09 | 11:30:00 AM | SA7-X1 | Lady (fleet) | Lady Skipper Series - Race 3 | score |
| Sat | 08/29/09 | 11:30:00 AM | SA7-P8 | Lady (fleet) | Lady Skipper Series - Race 4 | score |
| Sun | 08/30/09 | 11:30:00 AM | SA7-O1 | Comp (fleet) | Competition Series - Race 5 (Olympic) | score |
| Sun | 09/13/09 | 11:00:00 AM | 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 | 09/19/09 | 11:00:00 AM | SA7-S4 | Comm (fleet) | Commodores Cup - Race 1 | score |
| | | SA7-W4 | Comm (fleet) | Commodores Cup - Race 2 | score |
| Sun | 09/20/09 | 11:00:00 AM | SA7-O3 | Comm (fleet) | Commodores Cup - Race 3 | score |
| Sat | 09/26/09 | 11:00:00 AM | SA7-X7 | Open (fleet) | Goose Island MORF Open - Race 1 | score |
| | | SA7-Y7 | Open (fleet) | Goose Island MORF Open - Race 2 | score |
| Sun | 09/27/09 | 11:00:00 AM | SA7-X6 | Open (fleet) | Goose Island MORF Open - Race 3 | score |
| Wed | 09/30/09 | 11:30:00 AM | SA7 | Boty (fleet) | Boat of the Year | score |
| | | | Season (fleet) | Season Summary | score |
