53 Wins, 38 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/19/86 | Won | Chimacum 36 | Orting 33 | League | 6.723 |
| 01/13/87 | Won | Chimacum 43 | Port Townsend 39 | League | 12.707 |
| 12/15/87 | Lost | Chimacum 39 | Foster 52 | League | 0.077 |
| 01/19/88 | Won | Chimacum 41 | Steilacoom 35 | League | 3.628 |
| 01/29/88 | Won | Chimacum 50 | Port Townsend 42 | League | 4.244 |
| 12/13/88 | Won | Chimacum 48 | Foster 44 | League | 1.816 |
| 01/03/89 | Won | Chimacum 36 | Eatonville 32 | League | 1.999 |
| 01/17/89 | Lost | Chimacum 38 | Steilacoom 39 | League | 9.596 |
| 02/17/89 | Lost | Chimacum 36 | Port Townsend 40 | League | 7.753 |
| 02/21/89 | Lost | Chimacum 39 | Charles Wright 51 | Playoff | 10.552 |
| 11/30/89 | Lost | Chimacum 24 | Tacoma Baptist 25 | Non-league | 5.003 |
| 01/05/90 | Won | Chimacum 52 | Vashon Island 44 | League | 5.608 |
| 01/16/90 | Won | Chimacum 59 | Orting 58 | League | 0.121 |
| 02/06/90 | Won | Chimacum 50 | Port Townsend 45 | League | 8.675 |
| 02/09/90 | Lost | Chimacum 40 | Seattle Christian 49 | League | 4.090 |
| 02/16/90 | Lost | Chimacum 44 | Charles Wright 45 | League | 7.756 |
| 12/07/90 | Lost | Chimacum 24 | Bush 36 | Non-league | 3.412 |
| Lost | Chimacum L | Charles Wright W | League | 3.049 | |
| 01/07/92 | Won | Chimacum 43 | Seattle Christian 27 | League | 2.320 |
| 01/10/92 | Won | Chimacum 55 | Eatonville 54 | League | 21.886 |
| 01/14/92 | Won | Chimacum 49 | North Mason 45 | League | 13.015 |
| 01/08/93 | Won | Chimacum 53 | Seattle Christian 32 | League | 7.060 |
| 11/30/94 | Lost | Chimacum 26 | Quilcene 35 | Non-league | 3.208 |
| 01/16/96 | Won | Chimacum 55 | Charles Wright 38 | League | 2.821 |
| 12/14/96 | Lost | Chimacum 27 | Auburn Adventist 36 | Non-league | 10.557 |
| 12/18/98 | Lost | Chimacum 26 | Steilacoom 34 | Non-league | 1.714 |
| 01/05/99 | Lost | Chimacum 40 | Klahowya 53 | League | 17.263 |
| 02/16/99 | Won | Chimacum 56 | Bremerton 51 | League | 4.926 |
| 03/02/99 | Lost | Chimacum 41 | Steilacoom 54 | Playoff | 1.714 |
| 12/02/99 | Lost | Chimacum 44 | Charles Wright 47 | Non-league | 26.190 |
| 12/28/99 | Lost | Chimacum 49 | North Mason 53 | Non-league | 3.680 |
| 12/19/00 | Won | Chimacum 42 | North Mason 38 | Non-league | 1.557 |
| 12/28/00 | Won | Chimacum 45 | Coupeville 44 | Non-league | 12.041 |
| 01/12/01 | Lost | Chimacum 28 | Foster 40 | League | 0.194 |
| 01/16/01 | Won | Chimacum 44 | Orting 42 | League | 17.079 |
| 01/19/01 | Won | Chimacum 40 | Vashon Island 38 | League | 8.267 |
| 01/30/01 | Lost | Chimacum 42 | Foster 49 | League | 0.194 |
| 12/05/02 | Won | Chimacum 50 | Crescent 45 | Non-league | 9.228 |
| 01/15/03 | Lost | Chimacum 40 | Quilcene 46 | Non-league | 3.533 |
| 01/28/03 | Lost | Chimacum 40 | Klahowya 46 | League | 0.627 |
| 02/07/03 | Lost | Chimacum 38 | Foster 45 | League | 4.814 |
| 02/11/03 | Won | Chimacum 52 | North Mason 49 | League | 6.548 |
| 02/25/03 | Lost | Chimacum 35 | Foster 45 | Playoff | 4.814 |
| 12/05/03 | Won | Chimacum 56 | Crescent 53 | Non-league | 5.911 |
| 12/16/03 | Lost | Chimacum 49 | Quilcene 52 | Non-league | 1.794 |
| 01/09/04 | Lost | Chimacum 51 | Klahowya 54 | League | 11.468 |
| 01/16/04 | Won | Chimacum 43 | Sequim 39 | League | 6.060 |
| 01/23/04 | Won | Chimacum 59 | Foster 47 | League | 6.148 |
| 02/27/04 | Lost | Chimacum 46 | Vashon Island 50 | Playoff | 1.496 |
| 12/10/04 | Lost | Chimacum 41 | Granite Falls 47 | Non-league | 2.076 |
| 01/14/05 | Won | Chimacum 41 | Orting 40 | League | 4.863 |
| 01/18/05 | Lost | Chimacum 38 | Vashon Island 45 | League | 1.761 |
| 01/21/05 | Lost | Chimacum 43 | Seattle Christian 47 | League | 5.051 |
| 02/18/05 | Won | Chimacum 47 | Port Townsend 39 | Playoff | 7.887 |
| 03/05/05 | Won | Chimacum 42 | Orting 34 | Playoff | 4.863 |
| 12/06/05 | Won | Chimacum 64 | King's West 56 | Non-league | 3.148 |
| 12/09/05 | Won | Chimacum 45 | Granite Falls 40 | Non-league | 0.085 |
| 01/13/06 | Lost | Chimacum 33 | Orting 37 | League | 15.459 |
| 01/17/06 | Won | Chimacum 63 | Vashon Island 56 | League | 3.079 |
| 01/27/06 | Won | Chimacum 57 | Port Townsend 52 | League | 7.474 |
| 12/01/06 | Won | Chimacum 47 | North Mason 42 | Non-league | 0.454 |
| 11/28/07 | Won | Chimacum 50 | Coupeville 35 | Non-league | 1.155 |
| 12/27/07 | Lost | Chimacum 51 | Port Townsend 57 | Non-league | 6.852 |
| 12/01/08 | Won | Chimacum 50 | North Mason 46 | Non-league | 4.401 |
| 12/27/08 | Won | Chimacum 54 | Port Townsend 51 | Non-league | 4.737 |
| 02/25/09 | Won | Chimacum 48 | Bush 38 | Playoff | 4.492 |
| 12/07/09 | Won | Chimacum 31 | Port Townsend 26 | Non-league | 1.002 |
| 12/18/09 | Lost | Chimacum 26 | Charles Wright 32 | League | 1.276 |
| 01/11/10 | Won | Chimacum 32 | Port Townsend 20 | Non-league | 1.002 |
| 01/19/10 | Lost | Chimacum 24 | Orting 30 | League | 0.528 |
| 02/09/10 | Lost | Chimacum 30 | Orting 36 | League | 0.528 |
| 12/17/10 | Won | Chimacum 30 | Charles Wright 26 | League | 10.867 |
| 01/05/11 | Lost | Chimacum 17 | Crescent 46 | Non-league | 17.975 |
| 01/08/11 | Won | Chimacum 54 | Auburn Adventist 47 | Non-league | 3.526 |
| 12/07/11 | Won | Chimacum 47 | Forks 44 | Non-league | 7.841 |
| 12/16/11 | Won | Chimacum 56 | Charles Wright 50 | League | 14.634 |
| 12/29/12 | Won | Chimacum 41 | Seattle Academy 29 | Non-league | 0.838 |
| 01/10/14 | Won | Chimacum 36 | Vashon Island 29 | League | 17.274 |
| 01/31/14 | Won | Chimacum 37 | Life Christian 36 | League | 17.957 |
| 12/15/14 | Won | Chimacum 53 | Bremerton 42 | Non-league | 12.502 |
| 01/30/15 | Lost | Chimacum 39 | Port Townsend 43 | League | 3.026 |
| 02/03/15 | Won | Chimacum 56 | Klahowya 40 | League | 5.230 |
| 01/22/16 | Won | Chimacum 47 | Klahowya 40 | League | 6.821 |
| 12/28/16 | Lost | Chimacum 36 | Vashon Island 40 | Non-league | 1.246 |
| 01/17/17 | Won | Chimacum 42 | Port Townsend 28 | League | 1.392 |
| 01/21/17 | Lost | Chimacum 44 | Aberdeen 49 | Non-league | 2.402 |
| 12/08/17 | Won | Chimacum 44 | Port Townsend 41 | League | 4.342 |
| 01/10/18 | Won | Chimacum 28 | Coupeville 20 | League | 0.073 |
| 01/12/18 | Lost | Chimacum 36 | Klahowya 50 | League | 7.282 |
| 01/21/19 | Won | Chimacum 42 | Vashon Island 33 | Non-league | 1.569 |
| 01/02/20 | Won | Chimacum 29 | Vashon Island 22 | Non-league | 0.657 |
36 Wins, 28 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/06/02 | Lost | Chimacum 58 | Forks 60 | Non-league | 17.013 |
| 01/10/03 | Lost | Chimacum 50 | Vashon Island 54 | League | 9.576 |
| 01/28/03 | Lost | Chimacum 55 | Klahowya 61 | League | 9.375 |
| 02/07/03 | Lost | Chimacum 71 | Foster 75 | League | 5.146 |
| 02/21/03 | Lost | Chimacum 44 | Klahowya 47 | Playoff | 9.375 |
| 03/05/03 | Lost | Chimacum 53 | Eatonville 66 | Playoff | 3.674 |
| 12/12/03 | Lost | Chimacum 52 | Crescent 56 | Non-league | 17.648 |
| 12/15/03 | Won | Chimacum 61 | La Conner 47 | Non-league | 10.810 |
| 01/20/04 | Won | Chimacum 54 | Vashon Island 52 | League | 9.367 |
| 01/27/04 | Lost | Chimacum 49 | Port Townsend 53 | League | 0.918 |
| 12/29/04 | Won | Chimacum 68 | Forks 65 | Non-league | 6.098 |
| 01/18/05 | Won | Chimacum 67 | Vashon Island 65 | League | 11.852 |
| 01/25/05 | Won | Chimacum 66 | Steilacoom 60 | League | 6.794 |
| 02/01/05 | Won | Chimacum 64 | Life Christian 55 | League | 3.517 |
| 02/08/05 | Won | Chimacum 68 | North Mason 67 | League | 8.740 |
| 03/09/05 | Won | Chimacum 66 | Ridgefield 44 | Playoff | 6.379 |
| 03/10/05 | Won | Chimacum 53 | Nooksack Valley 46 | Playoff | 15.900 |
| 12/09/05 | Lost | Chimacum 56 | Granite Falls 68 | Non-league | 2.417 |
| 12/16/05 | Lost | Chimacum 56 | Sultan 57 | Non-league | 2.954 |
| 12/20/05 | Won | Chimacum 74 | Coupeville 65 | Non-league | 1.969 |
| 01/06/06 | Lost | Chimacum 64 | Foster 67 | League | 11.438 |
| 01/17/06 | Won | Chimacum 62 | Vashon Island 56 | League | 16.654 |
| 01/31/06 | Lost | Chimacum 55 | Life Christian 64 | League | 0.349 |
| 03/03/06 | Won | Chimacum 54 | Eatonville 51 | Playoff | 0.133 |
| 12/12/06 | Lost | Chimacum 46 | Coupeville 49 | Non-league | 8.538 |
| 12/16/06 | Lost | Chimacum 45 | Port Townsend 53 | Non-league | 2.739 |
| 01/05/07 | Won | Chimacum 60 | Seattle Christian 53 | League | 4.353 |
| 01/27/07 | Lost | Chimacum 65 | Klahowya 67 | Non-league | 2.572 |
| 11/28/07 | Won | Chimacum 76 | Coupeville 34 | Non-league | 10.060 |
| 12/07/07 | Lost | Chimacum 31 | Orting 70 | League | 3.424 |
| 02/01/08 | Won | Chimacum 69 | Washington 55 | Non-league | 0.839 |
| 12/04/09 | Lost | Chimacum 35 | Forks 42 | Non-league | 3.892 |
| 12/18/09 | Won | Chimacum 70 | Charles Wright 63 | League | 0.248 |
| 01/26/10 | Won | Chimacum 56 | Charles Wright 45 | League | 0.248 |
| 12/06/10 | Won | Chimacum 63 | Klahowya 47 | Non-league | 2.478 |
| 12/17/10 | Won | Chimacum 56 | Charles Wright 55 | League | 3.377 |
| 01/04/11 | Won | Chimacum 64 | Seattle Christian 58 | League | 14.849 |
| 01/18/11 | Lost | Chimacum 68 | Orting 75 | League | 3.836 |
| 12/07/11 | Won | Chimacum 45 | Forks 43 | Non-league | 2.703 |
| 12/13/11 | Won | Chimacum 60 | Cascade Christian (Puyallup) 53 | League | 13.429 |
| 12/16/11 | Won | Chimacum 62 | Charles Wright 49 | League | 1.158 |
| 01/13/12 | Lost | Chimacum 52 | Vashon Island 55 | League | 4.543 |
| 01/24/12 | Won | Chimacum 65 | Charles Wright 57 | League | 1.158 |
| 02/03/12 | Won | Chimacum 44 | Life Christian 42 | League | 4.507 |
| 02/07/12 | Lost | Chimacum 55 | Vashon Island 60 | League | 4.543 |
| 02/11/12 | Won | Chimacum 49 | Cedar Park Christian (Bothell) 48 | Playoff | 6.622 |
| 11/27/12 | Won | Chimacum 51 | Klahowya 43 | Non-league | 4.074 |
| 12/20/12 | Won | Chimacum 46 | Port Townsend 42 | Non-league | 4.947 |
| 01/19/13 | Won | Chimacum 72 | Life Christian 66 | League | 6.966 |
| 12/05/13 | Lost | Chimacum 67 | Klahowya 77 | Non-league | 9.209 |
| 12/27/13 | Won | Chimacum 70 | Port Townsend 64 | Non-league | 11.839 |
| 01/21/14 | Won | Chimacum 54 | Bellevue Christian 49 | League | 0.872 |
| 01/28/14 | Won | Chimacum 45 | Eatonville 42 | League | 9.031 |
| 01/07/15 | Won | Chimacum 56 | Port Angeles 49 | Non-league | 1.096 |
| 01/23/15 | Lost | Chimacum 50 | Klahowya 58 | League | 2.646 |
| 02/06/15 | Lost | Chimacum 68 | Coupeville 72 | League | 4.892 |
| 02/09/15 | Lost | Chimacum 50 | Port Townsend 59 | League | 5.629 |
| 01/16/16 | Won | Chimacum 71 | Forks 61 | Non-league | 1.112 |
| 01/19/16 | Lost | Chimacum 65 | Coupeville 72 | League | 9.723 |
| 01/29/16 | Won | Chimacum 58 | Port Townsend 56 | League | 2.716 |
| 02/06/16 | Won | Chimacum 43 | Port Townsend 40 | League | 2.716 |
| 01/27/17 | Lost | Chimacum 53 | Coupeville 56 | League | 4.342 |
| 01/31/17 | Lost | Chimacum 49 | Klahowya 58 | League | 5.986 |
| 11/29/17 | Lost | Chimacum 40 | Chief Kitsap 46 | Non-league | 2.770 |