58 Wins, 37 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/05/88 | Lost | Oak Harbor 43 | Bellingham 49 | Non-league | 2.744 |
| 12/12/88 | Won | Oak Harbor 49 | Everett 47 | League | 4.374 |
| 01/09/89 | Lost | Oak Harbor 38 | Snohomish 43 | League | 0.841 |
| 02/06/89 | Lost | Oak Harbor 40 | Snohomish 48 | League | 0.841 |
| 02/13/89 | Won | Oak Harbor 49 | Cascade (Everett) 45 | League | 3.629 |
| 02/22/89 | Won | Oak Harbor 67 | Everett 53 | League | 4.374 |
| 01/08/90 | Lost | Oak Harbor 46 | Marysville-Pilchuck 49 | League | 5.403 |
| 01/24/90 | Won | Oak Harbor 35 | Cascade (Everett) 34 | League | 5.039 |
| 01/29/90 | Won | Oak Harbor 47 | Everett 38 | League | 8.294 |
| 01/09/91 | Won | Oak Harbor W | Everett L | League | 12.743 |
| 01/30/91 | Won | Oak Harbor 46 | Cascade (Everett) 45 | League | 7.923 |
| 12/13/91 | Won | Oak Harbor 46 | Lynnwood 43 | Non-league | 8.425 |
| 01/15/92 | Won | Oak Harbor 39 | Cascade (Everett) 35 | League | 0.606 |
| 01/31/92 | Won | Oak Harbor 66 | Everett 64 | League | 4.375 |
| 02/05/92 | Won | Oak Harbor 44 | Snohomish 42 | League | 12.980 |
| 02/12/92 | Won | Oak Harbor 45 | Cascade (Everett) 44 | League | 0.606 |
| 02/19/92 | Lost | Oak Harbor 40 | Marysville-Pilchuck 42 | League | 4.117 |
| 01/13/93 | Won | Oak Harbor 54 | Cascade (Everett) 42 | League | 3.118 |
| 01/29/93 | Won | Oak Harbor 42 | Everett 41 | League | 0.840 |
| 12/10/93 | Won | Oak Harbor 45 | Mariner 34 | League | 1.697 |
| 12/17/93 | Won | Oak Harbor 50 | Marysville-Pilchuck 45 | League | 18.348 |
| 12/04/98 | Lost | Oak Harbor 41 | Squalicum 62 | Non-league | 1.980 |
| 12/14/98 | Lost | Oak Harbor 59 | Burlington-Edison 75 | Non-league | 0.080 |
| 12/30/98 | Won | Oak Harbor 60 | South Whidbey 59 | Non-league | 11.600 |
| 01/29/99 | Won | Oak Harbor 64 | Mountlake Terrace 57 | League | 2.122 |
| 02/05/99 | Won | Oak Harbor 56 | Marysville-Pilchuck 53 | League | 9.130 |
| 01/12/00 | Won | Oak Harbor 54 | Sehome 37 | League | 6.230 |
| 01/28/00 | Won | Oak Harbor 64 | Sehome 59 | League | 6.230 |
| 02/04/00 | Won | Oak Harbor 49 | Marysville-Pilchuck 45 | League | 10.627 |
| 02/18/00 | Lost | Oak Harbor 43 | Edmonds-Woodway 58 | League | 0.139 |
| 12/21/01 | Won | Oak Harbor 53 | Snohomish 40 | League | 6.122 |
| 02/06/02 | Lost | Oak Harbor 53 | Lake Stevens 58 | League | 3.415 |
| 12/06/02 | Lost | Oak Harbor 52 | Anacortes 65 | Non-league | 8.743 |
| 01/08/03 | Won | Oak Harbor 57 | Lake Stevens 56 | League | 4.552 |
| 01/17/03 | Won | Oak Harbor 59 | Monroe 53 | League | 6.282 |
| 01/29/03 | Won | Oak Harbor 46 | Snohomish 44 | League | 8.568 |
| 02/12/03 | Lost | Oak Harbor 53 | Cascade (Everett) 56 | League | 4.115 |
| 03/01/03 | Won | Oak Harbor 47 | Snohomish 43 | Playoff | 8.568 |
| 12/05/03 | Won | Oak Harbor 65 | Anacortes 59 | Non-league | 5.089 |
| 12/20/03 | Won | Oak Harbor 54 | Marysville-Pilchuck 46 | League | 0.202 |
| 01/12/04 | Won | Oak Harbor 54 | Lake Stevens 49 | League | 1.291 |
| 01/14/04 | Lost | Oak Harbor 53 | Mount Vernon 57 | League | 20.039 |
| 02/06/04 | Won | Oak Harbor 51 | Lake Stevens 42 | League | 1.291 |
| 02/11/04 | Lost | Oak Harbor 45 | Cascade (Everett) 65 | League | 5.876 |
| 02/13/04 | Lost | Oak Harbor 45 | Mount Vernon 60 | League | 20.039 |
| 02/28/04 | Won | Oak Harbor 48 | Everett 42 | Playoff | 2.209 |
| 12/29/04 | Won | Oak Harbor 45 | Sehome 36 | Non-league | 7.530 |
| 01/12/05 | Lost | Oak Harbor 43 | Stanwood 46 | League | 5.305 |
| 01/19/05 | Lost | Oak Harbor 58 | Marysville-Pilchuck 67 | League | 3.994 |
| 12/30/05 | Won | Oak Harbor 43 | Ferndale 40 | Non-league | 12.176 |
| 01/06/06 | Won | Oak Harbor 70 | Arlington 55 | League | 0.315 |
| 01/10/06 | Lost | Oak Harbor 30 | Stanwood 45 | League | 1.572 |
| 02/08/06 | Won | Oak Harbor 55 | Arlington 49 | League | 0.315 |
| 01/03/07 | Lost | Oak Harbor 29 | Stanwood 49 | League | 3.615 |
| 01/05/07 | Won | Oak Harbor 70 | Lake Stevens 65 | League | 4.278 |
| 02/06/07 | Won | Oak Harbor 56 | Monroe 30 | League | 3.106 |
| 02/17/07 | Lost | Oak Harbor 44 | Mountlake Terrace 52 | Playoff | 7.060 |
| 12/29/07 | Lost | Oak Harbor 30 | Federal Way 32 | Non-league | 12.186 |
| 02/06/08 | Lost | Oak Harbor 43 | Marysville-Pilchuck 47 | League | 5.328 |
| 12/06/08 | Lost | Oak Harbor 49 | Bellingham 54 | Non-league | 17.412 |
| 01/06/09 | Lost | Oak Harbor 49 | Arlington 52 | League | 2.600 |
| 01/14/09 | Won | Oak Harbor 49 | Marysville-Pilchuck 35 | League | 0.416 |
| 01/17/09 | Lost | Oak Harbor 50 | Everett 54 | League | 17.959 |
| 02/04/09 | Lost | Oak Harbor 39 | Arlington 48 | League | 2.600 |
| 02/18/09 | Won | Oak Harbor 52 | Jackson 51 | Playoff | 1.272 |
| 02/21/09 | Lost | Oak Harbor 34 | Kamiak 43 | Playoff | 3.669 |
| 02/25/09 | Won | Oak Harbor 52 | Edmonds-Woodway 46 | Playoff | 0.084 |
| 12/14/09 | Lost | Oak Harbor 33 | Snohomish 40 | League | 4.288 |
| 12/30/09 | Lost | Oak Harbor 47 | Eatonville 58 | Non-league | 0.786 |
| 01/07/10 | Won | Oak Harbor 49 | Stanwood 41 | League | 0.190 |
| 01/13/10 | Won | Oak Harbor 52 | Monroe 47 | League | 10.867 |
| 01/27/10 | Lost | Oak Harbor 34 | Everett 41 | League | 11.043 |
| 02/03/10 | Won | Oak Harbor 67 | Arlington 53 | League | 3.071 |
| 02/05/10 | Won | Oak Harbor 50 | Stanwood 48 | League | 0.190 |
| 02/12/10 | Lost | Oak Harbor 43 | Shorewood 51 | Playoff | 7.856 |
| 12/06/10 | Lost | Oak Harbor 40 | Squalicum 51 | Non-league | 0.831 |
| 12/30/10 | Won | Oak Harbor 51 | North Thurston 49 | Non-league | 7.942 |
| 01/26/11 | Won | Oak Harbor 46 | Mountlake Terrace 43 | League | 2.182 |
| 11/27/12 | Won | Oak Harbor 54 | Anacortes 51 | Non-league | 0.599 |
| 01/04/13 | Won | Oak Harbor 48 | Mountlake Terrace 44 | League | 12.589 |
| 01/06/14 | Lost | Oak Harbor 48 | Sedro-Woolley 56 | Non-league | 1.399 |
| 12/29/14 | Won | Oak Harbor 34 | Bellingham 32 | Non-league | 5.473 |
| 02/04/15 | Won | Oak Harbor 46 | Marysville-Getchell 43 | League | 15.402 |
| 12/02/15 | Won | Oak Harbor 56 | Mariner 46 | Non-league | 9.181 |
| 12/18/15 | Won | Oak Harbor 58 | Ferndale 50 | Non-league | 6.045 |
| 02/09/16 | Won | Oak Harbor 39 | Everett 38 | League | 3.449 |
| 02/10/16 | Won | Oak Harbor 43 | Everett 33 | Playoff | 3.449 |
| 12/20/16 | Won | Oak Harbor 36 | Cascade (Everett) 30 | Non-league | 4.588 |
| 01/11/17 | Lost | Oak Harbor 50 | Mountlake Terrace 53 | League | 2.590 |
| 12/19/17 | Won | Oak Harbor 36 | Cascade (Everett) 34 | Non-league | 0.776 |
| 12/28/17 | Won | Oak Harbor 44 | South Whidbey 33 | Non-league | 0.832 |
| 01/10/18 | Lost | Oak Harbor 36 | Mountlake Terrace 45 | League | 0.694 |
| 12/04/18 | Lost | Oak Harbor 44 | Marysville-Pilchuck 46 | Non-league | 4.603 |
| 01/10/19 | Lost | Oak Harbor 32 | Mountlake Terrace 42 | League | 1.827 |
| 01/17/19 | Lost | Oak Harbor 32 | Marysville-Pilchuck 36 | League | 4.603 |
50 Wins, 19 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 01/03/03 | Won | Oak Harbor 63 | Marysville-Pilchuck 61 | League | 9.560 |
| 01/07/03 | Won | Oak Harbor 57 | Lake Stevens 50 | League | 6.209 |
| 01/17/03 | Lost | Oak Harbor 80 | Monroe 88 | League | 1.815 |
| 01/31/03 | Won | Oak Harbor 82 | Arlington 78 | League | 5.913 |
| 02/07/03 | Won | Oak Harbor 61 | Lake Stevens 58 | League | 6.209 |
| 02/14/03 | Won | Oak Harbor 57 | Mount Vernon 53 | League | 12.508 |
| 01/09/04 | Won | Oak Harbor 51 | Cascade (Everett) 48 | League | 0.251 |
| 01/16/04 | Lost | Oak Harbor 73 | Monroe 81 | League | 2.400 |
| 01/23/04 | Won | Oak Harbor 83 | Stanwood 79 | League | 4.884 |
| 02/03/04 | Won | Oak Harbor 84 | Marysville-Pilchuck 82 | League | 2.942 |
| 02/06/04 | Won | Oak Harbor 71 | Lake Stevens 54 | League | 6.551 |
| 12/16/05 | Won | Oak Harbor 42 | Monroe 41 | League | 7.943 |
| 02/03/06 | Won | Oak Harbor 65 | Lake Stevens 47 | League | 0.435 |
| 12/22/06 | Lost | Oak Harbor 61 | Everett 70 | League | 4.256 |
| 02/06/07 | Lost | Oak Harbor 45 | Monroe 48 | League | 2.512 |
| 02/08/07 | Won | Oak Harbor 88 | Marysville-Pilchuck 85 | League | 13.211 |
| 12/07/07 | Won | Oak Harbor 71 | Cascade (Everett) 69 | League | 6.408 |
| 12/15/07 | Lost | Oak Harbor 60 | Coupeville 63 | Non-league | 8.912 |
| 01/12/08 | Won | Oak Harbor 66 | Cascade (Everett) 61 | League | 6.408 |
| 01/25/08 | Won | Oak Harbor 51 | Everett 45 | League | 3.117 |
| 12/27/08 | Lost | Oak Harbor 41 | Sedro-Woolley 53 | Non-league | 7.453 |
| 12/31/08 | Won | Oak Harbor 63 | Coupeville 51 | Non-league | 2.383 |
| 12/17/09 | Lost | Oak Harbor 58 | Everett 65 | League | 7.595 |
| 12/21/09 | Lost | Oak Harbor 61 | Coupeville 66 | Non-league | 1.543 |
| 01/14/10 | Won | Oak Harbor 63 | Monroe 44 | League | 3.489 |
| 12/02/10 | Won | Oak Harbor 47 | Marysville-Pilchuck 42 | Non-league | 1.307 |
| 12/10/10 | Lost | Oak Harbor 53 | Lynnwood 65 | League | 10.889 |
| 12/17/10 | Lost | Oak Harbor 48 | Everett 56 | League | 1.662 |
| 12/21/10 | Won | Oak Harbor 69 | Mountlake Terrace 62 | League | 9.766 |
| 12/29/10 | Lost | Oak Harbor 47 | South Kitsap 55 | Non-league | 0.945 |
| 01/18/11 | Won | Oak Harbor 48 | Shorewood 45 | League | 7.238 |
| 01/20/11 | Lost | Oak Harbor 62 | Everett 67 | League | 1.662 |
| 01/28/11 | Won | Oak Harbor 71 | Meadowdale 62 | League | 8.228 |
| 02/01/11 | Won | Oak Harbor 63 | Shorecrest 52 | League | 4.736 |
| 11/29/11 | Lost | Oak Harbor 52 | Cascade (Everett) 59 | Non-league | 3.559 |
| 12/20/11 | Won | Oak Harbor 52 | Meadowdale 46 | League | 0.964 |
| 01/24/12 | Lost | Oak Harbor 48 | Everett 60 | League | 3.183 |
| 01/26/12 | Won | Oak Harbor 43 | Meadowdale 42 | League | 0.964 |
| 02/08/12 | Won | Oak Harbor 57 | Shorewood 52 | Playoff | 15.631 |
| 12/29/12 | Won | Oak Harbor 55 | Nathan Hale 51 | Non-league | 2.472 |
| 01/02/13 | Lost | Oak Harbor 53 | Sedro-Woolley 56 | Non-league | 2.172 |
| 01/25/13 | Won | Oak Harbor 51 | Shorecrest 44 | League | 6.021 |
| 01/29/13 | Lost | Oak Harbor 56 | Marysville-Pilchuck 57 | League | 16.465 |
| 02/06/13 | Won | Oak Harbor 54 | Shorewood 49 | Playoff | 11.202 |
| 02/13/13 | Won | Oak Harbor 47 | Shorecrest 46 | Playoff | 6.021 |
| 01/03/14 | Won | Oak Harbor 58 | Marysville-Pilchuck 55 | League | 6.038 |
| 01/14/14 | Won | Oak Harbor 65 | Shorewood 54 | League | 7.659 |
| 01/28/14 | Won | Oak Harbor 49 | Everett 36 | League | 1.783 |
| 02/05/14 | Lost | Oak Harbor 51 | Marysville-Getchell 60 | League | 5.957 |
| 12/06/14 | Won | Oak Harbor 57 | Burlington-Edison 44 | Non-league | 5.372 |
| 01/16/15 | Won | Oak Harbor 70 | Marysville-Getchell 62 | League | 2.813 |
| 01/22/15 | Won | Oak Harbor 72 | Everett 69 | League | 2.091 |
| 12/29/15 | Won | Oak Harbor 53 | Sedro-Woolley 48 | Non-league | 6.253 |
| 01/29/16 | Won | Oak Harbor 62 | Arlington 61 | League | 10.976 |
| 02/08/16 | Won | Oak Harbor 70 | Everett 60 | League | 6.354 |
| 12/02/16 | Won | Oak Harbor 51 | Lakewood 44 | Non-league | 11.384 |
| 12/21/16 | Won | Oak Harbor 40 | South Whidbey 35 | Non-league | 9.261 |
| 01/31/17 | Won | Oak Harbor 54 | Burlington-Edison 51 | Non-league | 12.003 |
| 02/03/17 | Won | Oak Harbor 55 | Marysville-Pilchuck 48 | League | 17.859 |
| 12/20/17 | Won | Oak Harbor 57 | South Whidbey 53 | Non-league | 7.570 |
| 12/29/17 | Won | Oak Harbor 63 | Meridian 58 | Non-league | 8.640 |
| 01/02/18 | Won | Oak Harbor 61 | Shorewood 59 | League | 0.670 |
| 12/07/18 | Lost | Oak Harbor 52 | South Whidbey 65 | Non-league | 3.879 |
| 12/12/18 | Won | Oak Harbor 59 | Archbishop Murphy 53 | League | 2.909 |
| 12/22/18 | Won | Oak Harbor 70 | Bellingham 65 | Non-league | 6.874 |
| 01/04/19 | Won | Oak Harbor 66 | Cedarcrest 62 | League | 2.026 |
| 01/21/19 | Won | Oak Harbor 65 | Shorewood 55 | League | 4.170 |
| 01/23/19 | Won | Oak Harbor 50 | Snohomish 42 | League | 5.785 |
| 01/25/19 | Lost | Oak Harbor 45 | Everett 53 | League | 7.306 |