58 Wins, 57 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/12/86 | Won | Port Townsend 45 | Seattle Christian 41 | League | 5.878 |
| 12/16/86 | Lost | Port Townsend 47 | North Mason 51 | League | 0.755 |
| 12/19/86 | Lost | Port Townsend 32 | Vashon Island 44 | League | 3.881 |
| 01/13/87 | Lost | Port Townsend 39 | Chimacum 43 | League | 12.707 |
| 01/27/87 | Lost | Port Townsend 58 | North Mason 61 | League | 0.755 |
| 12/18/87 | Lost | Port Townsend 58 | Foster 62 | League | 4.320 |
| 12/30/87 | Won | Port Townsend 55 | Lynden 47 | Non-league | 9.707 |
| 01/08/88 | Won | Port Townsend 53 | Eatonville 49 | League | 0.524 |
| 01/26/88 | Lost | Port Townsend 30 | Steilacoom 41 | League | 0.615 |
| 01/29/88 | Lost | Port Townsend 42 | Chimacum 50 | League | 4.244 |
| 02/02/88 | Won | Port Townsend 59 | North Mason 55 | League | 8.791 |
| 01/10/89 | Lost | Port Townsend 44 | Vashon Island 45 | League | 2.841 |
| 01/17/89 | Lost | Port Townsend 36 | Charles Wright 41 | League | 2.799 |
| 02/10/89 | Won | Port Townsend 54 | Eatonville 34 | League | 9.752 |
| 02/14/89 | Lost | Port Townsend 39 | Steilacoom 49 | League | 1.843 |
| 02/17/89 | Won | Port Townsend 40 | Chimacum 36 | League | 7.753 |
| 01/16/90 | Won | Port Townsend 37 | North Mason 28 | League | 1.356 |
| 02/06/90 | Lost | Port Townsend 45 | Chimacum 50 | League | 8.675 |
| 02/20/90 | Won | Port Townsend 56 | North Mason 42 | Playoff | 1.356 |
| 02/23/91 | Lost | Port Townsend 29 | Vashon Island 33 | Playoff | 0.959 |
| 02/04/92 | Won | Port Townsend 53 | North Mason 33 | League | 2.920 |
| 02/18/92 | Won | Port Townsend 52 | Vashon Island 45 | League | 3.049 |
| 12/11/92 | Lost | Port Townsend 33 | Quilcene 35 | Non-league | 8.602 |
| 01/29/93 | Won | Port Townsend 43 | North Mason 39 | League | 6.053 |
| 12/17/93 | Lost | Port Townsend 36 | Seattle Christian 46 | League | 1.452 |
| 01/04/94 | Lost | Port Townsend 26 | Vashon Island 43 | League | 0.266 |
| 01/22/94 | Won | Port Townsend 33 | King's 32 | Non-league | 11.805 |
| 02/15/94 | Won | Port Townsend 44 | Eatonville 33 | League | 1.259 |
| 01/30/96 | Won | Port Townsend 38 | North Kitsap 34 | League | 0.106 |
| 02/09/96 | Won | Port Townsend 41 | Sequim 25 | League | 4.260 |
| 02/16/96 | Won | Port Townsend 55 | Bremerton 52 | League | 20.766 |
| 01/17/97 | Lost | Port Townsend 35 | Sequim 40 | League | 10.062 |
| 01/24/97 | Won | Port Townsend 46 | Bremerton 45 | League | 17.402 |
| 02/04/97 | Lost | Port Townsend 31 | North Kitsap 34 | League | 13.638 |
| 02/07/97 | Won | Port Townsend 49 | Bainbridge 37 | League | 6.237 |
| 02/11/97 | Lost | Port Townsend 35 | Central Kitsap 57 | League | 0.462 |
| 02/13/98 | Won | Port Townsend 57 | Olympic 49 | League | 2.282 |
| 03/06/98 | Lost | Port Townsend 28 | Eatonville 43 | Playoff | 3.985 |
| 03/07/98 | Lost | Port Townsend 45 | Vashon Island 49 | Playoff | 7.744 |
| 01/26/99 | Lost | Port Townsend 45 | North Kitsap 51 | League | 1.142 |
| 02/16/99 | Won | Port Townsend 45 | Central Kitsap 39 | League | 8.872 |
| 03/06/99 | Lost | Port Townsend 47 | Eatonville 56 | Playoff | 1.752 |
| 12/07/99 | Won | Port Townsend 40 | Central Kitsap 38 | League | 16.845 |
| 12/17/99 | Lost | Port Townsend 39 | Sequim 43 | League | 5.822 |
| 01/04/00 | Lost | Port Townsend 46 | Bremerton 47 | League | 13.454 |
| 02/15/00 | Lost | Port Townsend 61 | Olympic 62 | League | 9.400 |
| 01/26/01 | Won | Port Townsend 49 | North Kitsap 34 | League | 2.946 |
| 02/01/02 | Won | Port Townsend 36 | Sequim 35 | League | 2.940 |
| 02/12/02 | Lost | Port Townsend 51 | Vashon Island 58 | League | 0.812 |
| 02/14/02 | Lost | Port Townsend 39 | Foster 42 | League | 7.689 |
| 12/27/02 | Lost | Port Townsend 41 | Eastlake 50 | Non-league | 6.177 |
| 12/19/03 | Won | Port Townsend 53 | South Whidbey 47 | Non-league | 1.827 |
| 03/10/04 | Won | Port Townsend 42 | Chewelah 41 | Playoff | 15.465 |
| 12/29/04 | Won | Port Townsend 48 | South Whidbey 47 | Non-league | 3.771 |
| 01/18/05 | Lost | Port Townsend 40 | Life Christian 43 | League | 8.556 |
| 01/25/05 | Won | Port Townsend 53 | North Mason 52 | League | 0.576 |
| 02/01/05 | Won | Port Townsend 59 | Eatonville 46 | League | 6.218 |
| 02/11/05 | Lost | Port Townsend 33 | Cascade Christian (Puyallup) 35 | League | 5.924 |
| 02/18/05 | Lost | Port Townsend 39 | Chimacum 47 | Playoff | 7.887 |
| 03/02/05 | Lost | Port Townsend 26 | Orting 31 | Playoff | 3.024 |
| 01/03/06 | Lost | Port Townsend 39 | Vashon Island 46 | League | 4.394 |
| 01/27/06 | Lost | Port Townsend 52 | Chimacum 57 | League | 7.474 |
| 02/03/06 | Lost | Port Townsend 48 | Steilacoom 62 | League | 11.470 |
| 03/03/06 | Won | Port Townsend 38 | Foster 31 | Playoff | 0.949 |
| 03/04/06 | Lost | Port Townsend 44 | Vashon Island 46 | Playoff | 4.394 |
| 12/12/06 | Won | Port Townsend 55 | Port Angeles 43 | League | 3.710 |
| 02/02/07 | Won | Port Townsend 38 | Sequim 37 | League | 7.431 |
| 02/06/07 | Lost | Port Townsend 44 | North Mason 45 | League | 2.015 |
| 02/15/07 | Lost | Port Townsend 36 | North Mason 42 | Playoff | 2.015 |
| 02/21/07 | Won | Port Townsend 43 | Washington 39 | Playoff | 7.615 |
| 12/27/07 | Won | Port Townsend 57 | Chimacum 51 | Non-league | 6.852 |
| 12/29/07 | Won | Port Townsend 71 | Sequim 66 | Non-league | 12.385 |
| 01/04/08 | Won | Port Townsend 55 | Sequim 45 | League | 12.385 |
| 12/16/08 | Won | Port Townsend 73 | Olympic 66 | League | 3.246 |
| 12/27/08 | Lost | Port Townsend 51 | Chimacum 54 | Non-league | 4.737 |
| 02/03/09 | Lost | Port Townsend 51 | North Mason 64 | League | 0.336 |
| 12/07/09 | Lost | Port Townsend 26 | Chimacum 31 | Non-league | 1.002 |
| 01/11/10 | Lost | Port Townsend 20 | Chimacum 32 | Non-league | 1.002 |
| 01/29/10 | Won | Port Townsend 42 | North Kitsap 32 | League | 6.672 |
| 02/09/10 | Won | Port Townsend 41 | Klahowya 33 | League | 9.746 |
| 12/04/10 | Lost | Port Townsend 38 | Vashon Island 39 | Non-league | 5.188 |
| 12/07/10 | Lost | Port Townsend 45 | Sequim 54 | League | 3.792 |
| 12/17/10 | Won | Port Townsend 55 | Olympic 54 | League | 9.933 |
| 12/21/10 | Lost | Port Townsend 36 | North Mason 40 | League | 4.705 |
| 01/04/11 | Won | Port Townsend 43 | Bremerton 35 | League | 1.603 |
| 01/11/11 | Lost | Port Townsend 36 | Sequim 49 | League | 3.792 |
| 01/27/12 | Won | Port Townsend 37 | Olympic 33 | League | 19.378 |
| 12/04/12 | Lost | Port Townsend 45 | Kingston 47 | League | 3.565 |
| 12/14/12 | Won | Port Townsend 43 | North Kitsap 37 | League | 4.562 |
| 01/11/13 | Lost | Port Townsend 35 | Kingston 37 | League | 3.565 |
| 02/09/13 | Won | Port Townsend 52 | Charles Wright 49 | Non-league | 2.785 |
| 01/07/14 | Won | Port Townsend 46 | Bremerton 31 | League | 2.551 |
| 01/24/14 | Lost | Port Townsend 34 | North Mason 42 | League | 11.413 |
| 01/31/14 | Won | Port Townsend 50 | North Kitsap 49 | League | 8.462 |
| 02/04/14 | Won | Port Townsend 51 | Bremerton 43 | League | 2.551 |
| 02/15/14 | Won | Port Townsend 33 | Charles Wright 30 | Playoff | 11.264 |
| 01/27/15 | Won | Port Townsend 44 | Klahowya 43 | League | 8.255 |
| 01/30/15 | Won | Port Townsend 43 | Chimacum 39 | League | 3.026 |
| 12/08/15 | Lost | Port Townsend 46 | Quilcene 50 | Non-league | 10.518 |
| 01/13/16 | Lost | Port Townsend 42 | Klahowya 46 | League | 0.153 |
| 01/15/16 | Won | Port Townsend 43 | North Mason 33 | Non-league | 3.834 |
| 01/19/16 | Won | Port Townsend 40 | Bremerton 38 | Non-league | 9.559 |
| 02/04/16 | Lost | Port Townsend 38 | Klahowya 42 | League | 0.153 |
| 12/02/16 | Lost | Port Townsend 59 | North Mason 63 | Non-league | 2.455 |
| 12/29/16 | Won | Port Townsend 60 | Wahluke 55 | Non-league | 0.057 |
| 01/17/17 | Lost | Port Townsend 28 | Chimacum 42 | League | 1.392 |
| 01/31/17 | Won | Port Townsend 54 | Kingston 44 | Non-league | 16.393 |
| 12/08/17 | Lost | Port Townsend 41 | Chimacum 44 | League | 4.342 |
| 01/09/18 | Lost | Port Townsend 39 | Coupeville 40 | League | 4.269 |
| 02/14/18 | Won | Port Townsend 58 | Cascade Christian (Puyallup) 54 | Playoff | 16.051 |
| 01/15/19 | Won | Port Townsend 32 | Klahowya 24 | League | 3.978 |
| 01/31/19 | Won | Port Townsend 32 | Klahowya 20 | League | 3.978 |
| 01/10/20 | Won | Port Townsend 59 | Bear Creek 54 | Non-league | 6.599 |
| 01/18/20 | Lost | Port Townsend 30 | Granite Falls 37 | Non-league | 7.052 |
| 01/28/20 | Won | Port Townsend 58 | Clallam Bay 50 | Non-league | 5.749 |
37 Wins, 22 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 01/03/03 | Won | Port Townsend 54 | Klahowya 46 | League | 1.804 |
| 02/11/03 | Won | Port Townsend 82 | Vashon Island 55 | League | 1.603 |
| 12/09/03 | Won | Port Townsend 45 | King's West 38 | Non-league | 11.936 |
| 01/20/04 | Won | Port Townsend 70 | Klahowya 50 | League | 7.107 |
| 01/27/04 | Won | Port Townsend 53 | Chimacum 49 | League | 0.918 |
| 02/01/05 | Won | Port Townsend 60 | Eatonville 56 | League | 3.293 |
| 02/08/05 | Lost | Port Townsend 49 | Foster 50 | League | 2.906 |
| 03/01/05 | Lost | Port Townsend 64 | Orting 68 | Playoff | 6.832 |
| 01/10/06 | Lost | Port Townsend 48 | Sequim 57 | League | 1.061 |
| 01/17/06 | Won | Port Townsend 54 | Life Christian 45 | League | 7.451 |
| 02/07/06 | Lost | Port Townsend 50 | Foster 52 | League | 3.638 |
| 02/10/06 | Won | Port Townsend 58 | Orting 50 | League | 2.928 |
| 02/14/06 | Lost | Port Townsend 43 | Foster 60 | Playoff | 3.638 |
| 12/16/06 | Won | Port Townsend 53 | Chimacum 45 | Non-league | 2.739 |
| 12/29/06 | Lost | Port Townsend 56 | Archbishop Murphy 59 | Non-league | 0.474 |
| 01/09/07 | Won | Port Townsend 44 | Sequim 39 | League | 6.919 |
| 02/09/07 | Won | Port Townsend 47 | Klahowya 43 | League | 0.167 |
| 02/15/07 | Won | Port Townsend 50 | Klahowya 20 | Playoff | 0.167 |
| 03/02/07 | Lost | Port Townsend 39 | Fife 58 | Playoff | 1.152 |
| 01/04/08 | Lost | Port Townsend 46 | Sequim 56 | League | 12.737 |
| 03/05/08 | Won | Port Townsend 45 | West Valley (Spokane) 41 | Playoff | 7.998 |
| 03/06/08 | Won | Port Townsend 53 | River Ridge 47 | Playoff | 7.703 |
| 01/06/09 | Won | Port Townsend 49 | North Kitsap 42 | League | 2.551 |
| 02/03/09 | Won | Port Townsend 41 | North Mason 39 | League | 1.594 |
| 03/06/09 | Lost | Port Townsend 31 | King's 48 | Playoff | 3.369 |
| 12/15/09 | Won | Port Townsend 48 | Olympic 47 | League | 5.299 |
| 01/19/10 | Won | Port Townsend 42 | Kingston 37 | League | 9.686 |
| 01/29/10 | Won | Port Townsend 51 | North Kitsap 42 | League | 2.600 |
| 02/02/10 | Won | Port Townsend 43 | North Mason 29 | League | 12.032 |
| 12/03/10 | Lost | Port Townsend 44 | Klahowya 49 | League | 4.577 |
| 12/21/10 | Lost | Port Townsend 36 | North Mason 39 | League | 3.545 |
| 01/28/11 | Won | Port Townsend 63 | Olympic 58 | League | 5.256 |
| 12/12/12 | Lost | Port Townsend 45 | Klahowya 60 | League | 0.873 |
| 12/20/12 | Lost | Port Townsend 42 | Chimacum 46 | Non-league | 4.947 |
| 01/08/13 | Lost | Port Townsend 53 | Port Angeles 56 | League | 1.262 |
| 02/09/13 | Won | Port Townsend 44 | Seattle Christian 33 | Playoff | 17.861 |
| 02/12/13 | Won | Port Townsend 43 | Blaine 42 | Playoff | 10.762 |
| 12/11/13 | Lost | Port Townsend 29 | Kingston 38 | League | 0.797 |
| 12/27/13 | Lost | Port Townsend 64 | Chimacum 70 | Non-league | 11.839 |
| 12/28/13 | Won | Port Townsend 48 | La Conner 39 | Non-league | 3.903 |
| 01/17/14 | Lost | Port Townsend 36 | Kingston 38 | League | 0.797 |
| 01/06/15 | Won | Port Townsend 60 | Coupeville 51 | League | 0.737 |
| 01/27/15 | Won | Port Townsend 51 | Klahowya 48 | League | 2.983 |
| 02/09/15 | Won | Port Townsend 59 | Chimacum 50 | League | 5.629 |
| 01/15/16 | Won | Port Townsend 60 | North Mason 58 | Non-league | 1.101 |
| 01/29/16 | Lost | Port Townsend 56 | Chimacum 58 | League | 2.716 |
| 02/06/16 | Lost | Port Townsend 40 | Chimacum 43 | League | 2.716 |
| 12/19/16 | Won | Port Townsend 62 | South Whidbey 60 | Non-league | 2.757 |
| 12/29/16 | Won | Port Townsend 49 | Friday Harbor 39 | Non-league | 0.200 |
| 01/05/17 | Won | Port Townsend 73 | Forks 56 | Non-league | 1.209 |
| 01/27/17 | Won | Port Townsend 65 | Bremerton 51 | Non-league | 6.686 |
| 12/12/17 | Lost | Port Townsend 41 | Coupeville 44 | League | 13.420 |
| 01/19/18 | Lost | Port Townsend 51 | Klahowya 52 | League | 11.610 |
| 12/03/18 | Won | Port Townsend 50 | Bremerton 46 | Non-league | 8.174 |
| 12/28/18 | Won | Port Townsend 45 | Eastside Prep 40 | Non-league | 4.732 |
| 01/29/19 | Won | Port Townsend 63 | North Mason 54 | Non-league | 6.343 |
| 12/04/19 | Lost | Port Townsend 45 | Crosspoint 58 | Non-league | 4.489 |
| 12/28/19 | Won | Port Townsend 57 | Tyee 56 | Non-league | 11.593 |
| 01/18/20 | Won | Port Townsend 61 | Granite Falls 58 | Non-league | 0.818 |