| Sat | 5/17/2014 | 11:30 | SA7 | Perf (fleet) | Performance Series - Race 1 (Olympic) | score | |
| Wed | 5/21/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Tuneup Race | score | |
| Sat | 5/24/2014 | 11:30 | SA7 | Perf (fleet) | Performance Series - Race 2 (Trapezoid) | score | |
| Sun | 5/25/2014 | 11:30 | SA7 | Lady (fleet) | Lady Skipper Series - Race 1 (Olympic) | score | |
| Wed | 5/28/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 1 | score | |
| Sat | 5/31/2014 | 11:30 | SA7 | Perf (fleet) | Performance Series - Race 3 (Sprint) Crowleys | score | |
| | | SA7 | Perf (fleet) | Performance Series - Race 4 (Sprint) Crowleys | score | |
| | | | Sptx (fleet) | _Crowleys Sprint Regatta | score | |
| Sun | 6/01/2014 | 11:30 | SA7 | Lady (fleet) | Lady Skipper Series - Race 2 (Trapezoid) | score | |
| Wed | 6/04/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 2 | score | |
| Sat | 6/07/2014 | 10:00 | Zimmer | Long (fleet) | Long Distance Series - Race 1 (Zimmer) | score | |
| | 10:00 | Zimmer | Phrf (fleet) | PHRF Long Distance 1 | score | |
| Sun | 6/08/2014 | 11:30 | SA7 | Dble (fleet) | Double Handed Challenge | score | |
| | 11:30 | SA7 | Casu (fleet) | Drag Race | score | |
| | 11:30 | SA7 | Single (fleet) | Single Handed Challenge | score | |
| Wed | 6/11/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 3 | score | |
| Fri | 6/13/2014 | 19:00 | St. Joe | Long (fleet) | Long Distance Series - Race 2 (to St. Joe) | score | |
| | 19:00 | St. Joe | Phrf (fleet) | PHRF Long Distance 2 | score | |
| Sun | 6/15/2014 | 09:00 | St. Joe | Long (fleet) | Long Distance Series - Race 3 (from St. Joe) | score | |
| | 09:00 | St. Joe | Phrf (fleet) | PHRF Long Distance 3 | score | |
| Wed | 6/18/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 4 | score | |
| Sat | 6/21/2014 | 11:30 | SA7 | Perf (fleet) | Performance Series - Race 5 (Sprint) UK-Halsey | score | |
| | | SA7 | Perf (fleet) | Performance Series - Race 6 (Sprint) UK-Halsey | score | |
| | | SA7 | Spnt (fleet) | UK-Halsey Sprint Regatta | score | |
| Wed | 6/25/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 5 | score | |
| Sat | 6/28/2014 | 11:30 | SA7 | Perf (fleet) | Performance Series - Race 7 (Olympic) | score | |
| Wed | 7/02/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 6 | score | |
| Sun | 7/06/2014 | 11:30 | SA7 | Comp (fleet) | Competition Series - Race 1 (Trapezoid) Ulatowski | score | |
| Wed | 7/09/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 7 | score | |
| Sat | 7/12/2014 | | SA7 | Lady (fleet) | Lady Skipper Series - Race 3 (Btrap) | score | |
| Sun | 7/13/2014 | 11:30 | SA7 | Comp (fleet) | Competition Series - Race 2 (Olympic) | score | |
| Wed | 7/16/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 8 | score | |
| Sun | 7/27/2014 | 11:30 | SA7 | Casu (fleet) | Harbor Challenge - JAM ONLY FREE & Open to All | score | |
| Wed | 7/30/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 9 | score | |
| Sat | 8/02/2014 | | SA7 | Lady (fleet) | Lady Skipper Series - Race 4 (Btrap) | score | |
| | | SA7 | Lady (fleet) | Lady Skipper Series - Race 5 (W-L) | score | |
| Sun | 8/03/2014 | 11:30 | SA7 | Comp (fleet) | Competition Series - Race 3 (Sprint) Weathermark | score | |
| | | SA7 | Comp (fleet) | Competition Series - Race 4 (Sprint) Weathermark | score | |
| | | | Wmrk (fleet) | Weathermark Sprint Regatta | score | |
| Wed | 8/06/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 10 | score | |
| Sat | 8/09/2014 | 10:00 | MI City | Long (fleet) | Long Distance Series - Race 4 (to Michigan City) | score | |
| | 10:00 | MI City | Phrf (fleet) | PHRFection to Michigan City | score | |
| Sun | 8/10/2014 | 09:00 | MI City | Long (fleet) | Long Distance Series - Race 5 (from Michigan City) | score | |
| | 09:00 | MI City | Phrf (fleet) | PHRFection from Michigan City | score | |
| Wed | 8/13/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 11 | score | |
| Sun | 8/17/2014 | 11:30 | SA7 | Comp (fleet) | Competition Series - Race 5 (W-L) Marano by Skyway | score | |
| | | SA7 | Comp (fleet) | Competition Series - Race 6 (W-L) Marano by Skyway | score | |
| | | | Dmr (fleet) | Dominick Marano Regatta | score | |
| | | | Dmr (fleet) | Skyway Regatta | score | |
| Wed | 8/20/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 12 | score | |
| Sun | 8/24/2014 | | SA7 | Lady (fleet) | Lady Skipper Series - Race 6 (Btrap) | score | |
| | 11:30 | SA7 | Lady (fleet) | Lady Skipper Series - Race 7 (W-L) | score | |
| Wed | 8/27/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 13 | score | |
| Wed | 9/03/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 14 | score | |
| Sat | 9/06/2014 | 10:00 | Skippers | Long (fleet) | Long Distance Series - Race 6 (Skippers Club) | score | |
| Sun | 9/07/2014 | 11:30 | SA7 | Comp (fleet) | Competition Series - Race 7 (Trapezoid) | score | |
| Wed | 9/10/2014 | 18:40 | SA7 | Beer (fleet) | Beer Can - Race 15 | score | |
| Sat | 9/13/2014 | 11:30 | SA7 | Comm (fleet) | Commodores Cup - Race 1 | score | |
| | | SA7 | Comm (fleet) | Commodores Cup - Race 2 | score | |
| Sun | 9/14/2014 | 11:30 | SA7 | Comm (fleet) | Commodores Cup - Race 3 | score | |
| Sat | 9/20/2014 | 11:30 | SA7 | Open (fleet) | Goose Island MORF Open - Race 1 | score | |
| | 11:30 | SA7 | Opat (fleet) | Goose Island MORF Open - Race 1 Area-III | score | |
| | | SA7 | Open (fleet) | Goose Island MORF Open - Race 2 | score | |
| | | SA7 | Opat (fleet) | Goose Island MORF Open - Race 2 Area-III | score | |
| Sun | 9/21/2014 | 11:30 | SA7 | Open (fleet) | Goose Island MORF Open - Race 3 | score | |
| | 11:30 | SA7 | Opat (fleet) | Goose Island MORF Open - Race 3 Area-III | score | |
| Mon | 9/22/2014 | | | Boty (fleet) | Boat of the Year | score | |
| | | | Season (fleet) | Season Summary | score | |
