39 Wins, 29 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/02/86 | Lost | Highline 44 | Lincoln 45 | Non-league | 1.456 |
| 12/30/86 | Lost | Highline 37 | Newport (Bellevue) 39 | Non-league | 4.267 |
| 01/16/87 | Lost | Highline 43 | Hazen 46 | League | 6.142 |
| 02/11/87 | Lost | Highline 56 | Hazen 57 | Playoff | 6.142 |
| 12/05/87 | Won | Highline 45 | Lincoln 38 | Non-league | 8.609 |
| 02/02/88 | Won | Highline 49 | Hazen 45 | League | 10.210 |
| 12/16/89 | Won | Highline 50 | Foster 43 | Non-league | 2.401 |
| 01/05/90 | Won | Highline W | Renton L | League | 7.728 |
| 01/19/90 | Won | Highline 46 | Mount Rainier 44 | League | 7.672 |
| 02/06/90 | Lost | Highline 38 | Evergreen (Highline) 42 | League | 5.709 |
| 12/14/90 | Won | Highline 42 | Lindbergh 30 | League | 15.117 |
| 12/18/90 | Won | Highline W | Tyee L | League | 2.632 |
| 01/18/91 | Lost | Highline 41 | Mount Rainier 47 | League | 0.643 |
| 01/19/91 | Lost | Highline L | Liberty (Issaquah) W | League | 6.793 |
| 02/05/91 | Won | Highline 52 | Evergreen (Highline) 51 | League | 13.073 |
| 12/06/91 | Lost | Highline 35 | Renton 37 | League | 16.336 |
| 12/07/91 | Won | Highline 52 | Jefferson 34 | Non-league | 4.001 |
| 02/11/92 | Lost | Highline 34 | Lindbergh 37 | League | 6.379 |
| 02/14/92 | Won | Highline 53 | Tyee 35 | League | 6.021 |
| 02/18/92 | Lost | Highline 30 | Mount Si 34 | League | 5.945 |
| 01/18/94 | Won | Highline 42 | Lindbergh 39 | League | 10.180 |
| 01/13/95 | Won | Highline W | Renton L | League | 1.893 |
| 01/05/96 | Lost | Highline 34 | Renton 37 | League | 11.718 |
| 01/12/96 | Lost | Highline 39 | Lindbergh 44 | League | 2.892 |
| 02/17/96 | Lost | Highline 44 | Lindbergh 55 | Playoff | 2.892 |
| 02/20/96 | Lost | Highline 43 | Eastside Catholic 48 | Playoff | 1.362 |
| 01/07/97 | Won | Highline 47 | Kennedy 38 | League | 7.911 |
| 01/21/97 | Lost | Highline 31 | Mount Rainier 37 | League | 7.695 |
| 02/13/97 | Lost | Highline 39 | Liberty (Issaquah) 42 | League | 8.385 |
| 12/18/97 | Lost | Highline 40 | Renton 47 | League | 1.035 |
| 12/12/98 | Lost | Highline 32 | Vashon Island 45 | Non-league | 10.022 |
| 01/12/99 | Won | Highline 50 | Mount Rainier 44 | League | 11.979 |
| 01/19/99 | Won | Highline 61 | Hazen 53 | League | 10.476 |
| 02/20/99 | Won | Highline 61 | Renton 32 | Playoff | 0.815 |
| 12/10/99 | Won | Highline 39 | Vashon Island 36 | Non-league | 0.776 |
| 12/14/00 | Won | Highline 43 | Evergreen (Highline) 33 | League | 1.600 |
| 01/30/01 | Won | Highline 46 | Tyee 39 | League | 3.277 |
| 02/08/01 | Won | Highline 56 | Renton 52 | Playoff | 5.316 |
| 01/15/02 | Won | Highline 50 | Hazen 43 | League | 11.493 |
| 12/12/03 | Won | Highline 38 | Tyee 27 | League | 22.110 |
| 01/09/04 | Won | Highline 43 | Lindbergh 40 | League | 14.107 |
| 01/13/04 | Lost | Highline 40 | Evergreen (Highline) 42 | League | 2.174 |
| 01/27/04 | Lost | Highline 34 | Hazen 41 | League | 1.801 |
| 02/06/04 | Lost | Highline 56 | Evergreen (Highline) 63 | League | 2.174 |
| 11/30/04 | Lost | Highline 44 | Fife 56 | Non-league | 5.947 |
| 01/24/05 | Won | Highline 63 | Evergreen (Highline) 60 | League | 4.825 |
| 01/31/06 | Won | Highline 35 | Renton 33 | League | 11.644 |
| 01/26/07 | Lost | Highline 39 | Renton 41 | League | 0.611 |
| 01/25/08 | Won | Highline 47 | Renton 46 | League | 20.229 |
| 12/05/08 | Lost | Highline 37 | Tyee 40 | League | 13.664 |
| 12/21/09 | Lost | Highline 41 | Decatur 45 | Non-league | 2.290 |
| 12/28/09 | Won | Highline 32 | Eastside Catholic 30 | Non-league | 11.626 |
| 02/03/10 | Lost | Highline 27 | Evergreen (Highline) 30 | League | 12.406 |
| 01/21/11 | Won | Highline 42 | Hazen 40 | League | 17.687 |
| 12/09/11 | Won | Highline 50 | Foster 47 | League | 2.198 |
| 12/19/11 | Won | Highline 65 | Sammamish 49 | Non-league | 2.820 |
| 01/25/12 | Won | Highline 41 | Lindbergh 32 | League | 4.760 |
| 12/04/12 | Won | Highline 39 | Decatur 29 | Non-league | 0.532 |
| 01/23/13 | Lost | Highline 29 | Evergreen (Highline) 32 | League | 2.677 |
| 01/30/15 | Won | Highline 40 | Foster 35 | League | 1.915 |
| 02/04/15 | Won | Highline 59 | Lindbergh 58 | League | 6.686 |
| 01/08/16 | Won | Highline 54 | Lindbergh 52 | League | 20.307 |
| 12/13/16 | Won | Highline 49 | Orting 38 | League | 0.979 |
| 01/11/17 | Won | Highline 50 | Orting 29 | League | 0.979 |
| 01/24/17 | Won | Highline 35 | Steilacoom 29 | League | 3.964 |
| 12/15/17 | Won | Highline 53 | River Ridge 42 | League | 17.802 |
| 01/16/18 | Lost | Highline 33 | Tyee 39 | League | 7.185 |
| 12/07/18 | Lost | Highline 29 | Tyee 33 | League | 2.161 |
32 Wins, 24 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/11/02 | Won | Highline 59 | Washington 57 | Non-league | 5.707 |
| 12/20/02 | Won | Highline 75 | Lindbergh 70 | League | 5.930 |
| 01/04/03 | Lost | Highline 58 | Cedarcrest 67 | Non-league | 4.392 |
| 01/31/03 | Lost | Highline 45 | Mount Rainier 54 | League | 3.402 |
| 12/12/03 | Won | Highline 43 | Tyee 37 | League | 4.195 |
| 12/06/04 | Lost | Highline 52 | Foster 61 | Non-league | 3.455 |
| 01/18/05 | Won | Highline 31 | Hazen 21 | League | 9.243 |
| 01/24/05 | Won | Highline 46 | Evergreen (Highline) 37 | League | 0.594 |
| 01/28/05 | Won | Highline 55 | Lindbergh 51 | League | 10.201 |
| 11/29/05 | Won | Highline 69 | Fife 59 | Non-league | 2.272 |
| 12/20/05 | Lost | Highline 49 | Foster 53 | Non-league | 0.768 |
| 01/13/06 | Won | Highline 56 | Tyee 36 | League | 0.132 |
| 01/23/07 | Lost | Highline 56 | Evergreen (Highline) 60 | League | 3.222 |
| 02/08/08 | Won | Highline 63 | Lindbergh 46 | League | 0.337 |
| 02/14/08 | Lost | Highline 52 | Auburn Riverside 58 | Playoff | 0.468 |
| 01/20/09 | Won | Highline 57 | Lindbergh 52 | League | 3.581 |
| 12/05/09 | Lost | Highline 48 | Ingraham 58 | Non-league | 4.055 |
| 01/06/10 | Won | Highline 64 | Evergreen (Highline) 59 | League | 3.203 |
| 02/03/10 | Won | Highline 53 | Evergreen (Highline) 38 | League | 3.203 |
| 02/05/10 | Won | Highline 52 | Hazen 46 | League | 7.550 |
| 11/30/10 | Won | Highline 50 | Cleveland 45 | Non-league | 4.052 |
| 12/14/10 | Won | Highline 51 | Lindbergh 48 | League | 9.460 |
| 01/04/12 | Lost | Highline 55 | Tyee 56 | League | 4.036 |
| 12/07/12 | Won | Highline 64 | Tyee 61 | League | 1.405 |
| 01/04/13 | Won | Highline 49 | Foster 46 | League | 23.434 |
| 12/13/13 | Won | Highline 60 | Tyee 58 | League | 0.071 |
| 01/24/14 | Won | Highline 61 | Tyee 59 | League | 0.071 |
| 12/01/14 | Lost | Highline 62 | Ingraham 70 | Non-league | 1.592 |
| 12/15/14 | Won | Highline 74 | Decatur 72 | Non-league | 10.257 |
| 12/19/14 | Lost | Highline 56 | Evergreen (Highline) 59 | League | 1.257 |
| 01/07/15 | Lost | Highline 40 | Foster 49 | League | 2.035 |
| 01/20/15 | Won | Highline 57 | Seattle Christian 45 | Non-league | 2.600 |
| 01/21/15 | Lost | Highline 46 | Tyee 55 | League | 7.126 |
| 01/30/15 | Lost | Highline 40 | Foster 43 | League | 2.035 |
| 12/02/15 | Lost | Highline 61 | Nathan Hale 67 | Non-league | 6.429 |
| 12/07/15 | Lost | Highline 54 | Bellevue Christian 64 | Non-league | 10.334 |
| 12/09/15 | Won | Highline 66 | Kennedy Catholic 59 | League | 21.975 |
| 12/16/15 | Won | Highline 71 | Hazen 67 | League | 7.620 |
| 01/16/16 | Lost | Highline 44 | Seattle Christian 45 | Non-league | 4.578 |
| 01/27/16 | Lost | Highline 40 | Evergreen (Highline) 52 | League | 7.882 |
| 11/29/16 | Lost | Highline 64 | Lynnwood 80 | Non-league | 0.804 |
| 12/07/16 | Lost | Highline 44 | Evergreen (Highline) 49 | Non-league | 1.298 |
| 12/16/16 | Won | Highline 62 | River Ridge 61 | League | 9.559 |
| 12/20/16 | Won | Highline 67 | Clover Park 62 | League | 1.677 |
| 01/13/17 | Lost | Highline 55 | Tyee 63 | League | 9.005 |
| 01/20/17 | Won | Highline 66 | River Ridge 58 | League | 9.559 |
| 01/27/17 | Won | Highline 76 | Renton 72 | League | 8.345 |
| 11/28/17 | Won | Highline 66 | Lynnwood 61 | Non-league | 0.340 |
| 12/22/17 | Won | Highline 60 | Mount Rainier 52 | Non-league | 3.960 |
| 01/03/18 | Lost | Highline 50 | Seattle Christian 62 | Non-league | 4.230 |
| 12/05/18 | Lost | Highline 47 | Charles Wright 65 | Non-league | 8.568 |
| 12/13/18 | Won | Highline 68 | Seattle Christian 53 | Non-league | 2.921 |
| 12/09/19 | Won | Highline 67 | Cascade (Everett) 52 | Non-league | 4.116 |
| 12/19/19 | Lost | Highline 61 | Evergreen (Highline) 62 | League | 2.089 |
| 01/08/20 | Won | Highline 49 | Charles Wright 32 | Non-league | 1.674 |
| 01/20/20 | Lost | Highline 51 | Tyee 66 | League | 10.416 |