| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Island Cup - GOLD | Oak Harbor | Skipper | 14/21 (A Div) |
It appears Jack Knowles has not participated in any regattas this season.
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Cascadia Cup - Gold | Sail Sand Point | Skipper | 9/24 (B Div) | |
| Bellingham Regional | Bellingham Bay | Skipper | 7/13 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 NWISA Fleet Race Championships | Anacortes on Fidalgo Bay | Skipper | 17/20 (A Div) | |
| Islands Cup 2019 | Orcas | Skipper | 13/20 (A Div) | |
| NWISA Ranking Regatta #2 | Oak Harbor | Skipper | 14/20 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| NWISA Fall Championships- Ranking Regatta #1 | Lincoln OR | Skipper | 13/14 (A Div) | |
| Trick or Treat Team Race | Sail Orcas | Skipper | 8/12 | |
| Cascadia Cup - GOLD | Sail Sand Point | Skipper | 20/22 (A Div) | |
| NWISA North Regionals | Bellingham | Skipper | 9/16 (A Div) | |
| Burke Thomas Trophy - Radial | Lincoln OR | Skipper | 4/15 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| NWISA JV Team Race Districts | Central Kitsap | Crew | 9/14 | |
| NWISA Fleet Race Championship | Sail Sand Point | Skipper | 17/20 (A Div) | |
| ISLANDS CUP | San Juan Island Sailing Foundation | Skipper | 13/16 (A Div) | |
| Forrest Cook Regatta - Ranking Regatta #3 | Hood River | Skipper | 5/12 (A Div) | |
| Oak Harbor Team Race | Oak Harbor | Skipper | 3/9 | |
| Quartermaster Ranking Regatta (GOLD) | Bellarmine/Charles Wright/Gig Harbor | Skipper | 16/19 (A Div) | |
| SSP Combined Division - SILVER | Sail Sand Point | Skipper | 4/16 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Olympia: Fall Ranking Championship, Gold | Capital/Olympia | Skipper | 10/11 (B Div) | |
| Cascadia Cup - GOLD | Sail Sand Point | Skipper | 21/21 (A Div) | |
| NWISA North Regional | Oak Harbor | Skipper | 4/12 (A Div) | |
| NWISA Singlehand Champs - FULL | Unregistered-NWISA | Skipper | 6/7 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| NWISA Doublehanded Districts | West Sound, Orcas WA | Skipper | 12/17 (B Div) | |
| Island Cup Gold | Oak Harbor Yacht Club | Skipper | 9/14 (B Div) | |
| SSP Combined - SILVER | Sail Sand Point | Skipper | 5/14 | |
| NWISA North Regionals | Anacortes | Skipper | 9/14 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Olympia Regatta | Olympia Yacht Club | Crew | 17/19 (A Div) |