45 Wins, 32 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/09/86 | Won | Highland 40 | Kittitas 36 | Non-league | 8.031 |
| 12/11/87 | Won | Highland 50 | White Swan 40 | Non-league | 5.015 |
| 12/29/87 | Won | Highland 57 | Othello 47 | Non-league | 1.055 |
| 01/30/88 | Lost | Highland 36 | Zillah 40 | League | 2.349 |
| 12/17/88 | Won | Highland 41 | Toppenish 40 | League | 0.859 |
| 12/23/89 | Won | Highland 40 | White Swan 37 | Non-league | 8.974 |
| 12/28/91 | Lost | Highland 32 | Kittitas 35 | Non-league | 4.903 |
| 12/18/92 | Won | Highland 50 | Columbia (Burbank) 45 | Non-league | 0.007 |
| 12/22/92 | Lost | Highland 39 | Kittitas 42 | Non-league | 1.608 |
| 01/08/93 | Won | Highland 44 | Kiona-Benton 43 | Non-league | 1.325 |
| 01/22/93 | Won | Highland 40 | Columbia (Burbank) 38 | Non-league | 0.007 |
| 02/05/93 | Won | Highland 51 | Kiona-Benton 44 | Non-league | 1.325 |
| 02/09/93 | Won | Highland W | Naches Valley L | League | 0.404 |
| 12/14/93 | Lost | Highland 42 | Davis 43 | Non-league | 18.344 |
| 01/22/94 | Lost | Highland 39 | Wapato 41 | League | 3.181 |
| 12/16/94 | Won | Highland 40 | Zillah 39 | Non-league | 8.833 |
| 01/27/96 | Won | Highland 52 | Goldendale 51 | League | 12.143 |
| 02/22/96 | Won | Highland 47 | Zillah 32 | Playoff | 2.928 |
| 12/17/96 | Won | Highland 59 | East Valley (Yakima) 50 | Non-league | 2.869 |
| 12/20/96 | Lost | Highland 44 | Columbia (Burbank) 49 | Non-league | 7.731 |
| 01/24/97 | Lost | Highland 40 | Zillah 47 | League | 1.430 |
| 02/07/97 | Won | Highland 67 | Cle Elum-Roslyn 51 | League | 0.759 |
| 02/18/97 | Won | Highland 60 | Cle Elum-Roslyn 54 | Playoff | 0.759 |
| 02/21/97 | Won | Highland 45 | Royal 43 | Playoff | 1.489 |
| 02/06/98 | Won | Highland 44 | Warden 37 | League | 9.603 |
| 02/07/98 | Won | Highland 70 | Royal 50 | League | 1.683 |
| 12/04/98 | Lost | Highland 46 | Naches Valley 49 | Non-league | 1.748 |
| 01/30/99 | Won | Highland 66 | Kittitas 55 | League | 4.886 |
| 02/06/99 | Won | Highland 57 | Royal 48 | League | 0.863 |
| 02/19/99 | Won | Highland 46 | Zillah 44 | Playoff | 9.176 |
| 03/04/99 | Won | Highland 46 | Tonasket 33 | Playoff | 5.436 |
| 12/10/99 | Won | Highland 49 | Wahluke 22 | Non-league | 3.345 |
| 12/08/00 | Lost | Highland 41 | Wahluke 44 | Non-league | 13.121 |
| 01/26/01 | Won | Highland 44 | Cle Elum-Roslyn 32 | League | 4.825 |
| 01/27/01 | Won | Highland 57 | Granger 52 | League | 5.902 |
| 02/06/03 | Won | Highland 45 | Zillah 39 | League | 18.204 |
| 01/08/05 | Lost | Highland 38 | Goldendale 50 | League | 4.136 |
| 01/15/05 | Won | Highland 50 | Cle Elum-Roslyn 38 | League | 1.778 |
| 01/28/05 | Lost | Highland 30 | Goldendale 42 | League | 4.136 |
| 02/04/05 | Won | Highland 42 | Cle Elum-Roslyn 39 | League | 1.778 |
| 02/05/05 | Won | Highland 53 | Granger 36 | League | 3.809 |
| 01/21/06 | Won | Highland 53 | Zillah 49 | League | 14.479 |
| 02/03/06 | Lost | Highland 36 | Cle Elum-Roslyn 40 | League | 0.752 |
| 02/04/06 | Lost | Highland 50 | Granger 58 | League | 3.875 |
| 01/13/07 | Lost | Highland 50 | Mabton 54 | League | 6.604 |
| 01/27/07 | Lost | Highland 42 | White Swan 46 | League | 10.075 |
| 12/07/07 | Won | Highland 42 | Columbia (Burbank) 31 | Non-league | 16.853 |
| 12/14/07 | Lost | Highland 53 | Royal 58 | Non-league | 11.068 |
| 12/21/07 | Lost | Highland 36 | Naches Valley 48 | League | 2.273 |
| 01/04/08 | Lost | Highland 41 | White Swan 45 | League | 0.766 |
| 01/12/08 | Won | Highland 65 | Mabton 50 | League | 1.296 |
| 01/26/08 | Lost | Highland 35 | White Swan 49 | League | 0.766 |
| 02/02/08 | Won | Highland 39 | Zillah 35 | League | 13.375 |
| 12/03/08 | Lost | Highland 37 | Selah 42 | Non-league | 2.356 |
| 12/20/08 | Won | Highland 41 | Goldendale 32 | League | 3.526 |
| 02/12/09 | Lost | Highland 39 | Cle Elum-Roslyn 47 | League | 16.748 |
| 01/12/10 | Lost | Highland 29 | Riverside Christian 31 | Non-league | 5.135 |
| 02/11/10 | Lost | Highland 37 | Cle Elum-Roslyn 49 | League | 2.181 |
| 12/07/10 | Won | Highland 36 | Kittitas 23 | Non-league | 6.576 |
| 02/06/12 | Won | Highland 52 | Zillah 46 | League | 25.230 |
| 02/01/13 | Won | Highland 48 | Granger 37 | League | 24.205 |
| 01/18/14 | Won | Highland 34 | Cle Elum-Roslyn 23 | League | 10.647 |
| 01/25/14 | Won | Highland 36 | Goldendale 34 | League | 4.316 |
| 01/03/15 | Lost | Highland 30 | Goldendale 37 | League | 0.702 |
| 01/07/15 | Won | Highland 42 | Columbia (White Salmon) 21 | Non-league | 5.894 |
| 12/08/15 | Lost | Highland 43 | River View 46 | Non-league | 4.744 |
| 12/15/15 | Lost | Highland 45 | White Swan 46 | Non-league | 3.347 |
| 12/30/15 | Lost | Highland 36 | Columbia (White Salmon) 38 | Non-league | 9.162 |
| 01/14/17 | Lost | Highland 38 | Goldendale 43 | League | 5.109 |
| 12/01/17 | Won | Highland 51 | River View 46 | Non-league | 12.870 |
| 12/12/17 | Lost | Highland 48 | Goldendale 53 | League | 15.318 |
| 12/21/17 | Lost | Highland 36 | Wahluke 52 | Non-league | 0.579 |
| 01/23/18 | Won | Highland 51 | Naches Valley 33 | League | 0.208 |
| 01/05/19 | Lost | Highland 45 | Naches Valley 58 | League | 2.481 |
| 12/21/19 | Won | Highland 36 | Granger 28 | League | 3.853 |
| 12/28/19 | Lost | Highland 44 | Kittitas-Thorp 45 | Non-league | 1.442 |
| 02/07/20 | Won | Highland 47 | Cle Elum-Roslyn 41 | League | 13.915 |
43 Wins, 29 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/13/02 | Lost | Highland 65 | Columbia (Burbank) 66 | Non-league | 10.215 |
| 01/04/03 | Lost | Highland 45 | River View 51 | Non-league | 2.062 |
| 01/11/03 | Won | Highland 58 | Granger 45 | League | 4.376 |
| 01/18/03 | Lost | Highland 69 | Cle Elum-Roslyn 71 | League | 11.204 |
| 01/25/03 | Won | Highland 57 | White Swan 53 | League | 5.074 |
| 02/06/03 | Won | Highland 68 | Zillah 56 | League | 1.470 |
| 02/14/03 | Won | Highland 67 | White Swan 66 | League | 5.074 |
| 12/12/03 | Won | Highland 47 | Columbia (Burbank) 39 | Non-league | 2.399 |
| 12/13/03 | Lost | Highland 41 | Dayton 43 | Non-league | 4.284 |
| 12/16/03 | Won | Highland 63 | Naches Valley 61 | Non-league | 7.933 |
| 12/18/03 | Lost | Highland 41 | Royal 50 | Non-league | 4.208 |
| 12/27/03 | Lost | Highland 40 | La Salle 48 | Non-league | 1.294 |
| 12/30/03 | Won | Highland 58 | Cascade (Leavenworth) 56 | Non-league | 2.151 |
| 01/03/04 | Lost | Highland 61 | Warden 64 | Non-league | 8.567 |
| 01/24/04 | Won | Highland 58 | White Swan 54 | League | 9.208 |
| 01/31/04 | Lost | Highland 55 | Goldendale 58 | League | 0.198 |
| 02/13/04 | Won | Highland 55 | White Swan 53 | League | 9.208 |
| 02/17/04 | Won | Highland 57 | Columbia (Burbank) 52 | Playoff | 2.399 |
| 12/10/04 | Won | Highland 54 | Columbia (Burbank) 45 | Non-league | 4.695 |
| 12/11/04 | Lost | Highland 77 | Warden 83 | Non-league | 13.957 |
| 12/30/04 | Lost | Highland 66 | Liberty Bell 77 | Non-league | 5.128 |
| 01/28/05 | Won | Highland 56 | Goldendale 54 | League | 2.513 |
| 12/16/05 | Lost | Highland 44 | Royal 53 | Non-league | 2.992 |
| 12/29/05 | Lost | Highland 41 | La Salle 46 | Non-league | 5.288 |
| 01/28/06 | Lost | Highland 53 | White Swan 63 | League | 8.361 |
| 02/03/06 | Lost | Highland 56 | Cle Elum-Roslyn 62 | League | 12.590 |
| 02/14/06 | Won | Highland 57 | Wahluke 55 | Playoff | 7.410 |
| 12/01/06 | Lost | Highland 48 | Kiona-Benton 52 | Non-league | 2.478 |
| 12/15/06 | Lost | Highland 52 | Royal 54 | Non-league | 2.010 |
| 12/22/06 | Won | Highland 53 | Naches Valley 51 | League | 5.890 |
| 01/05/07 | Won | Highland 64 | White Swan 43 | League | 0.902 |
| 01/06/07 | Won | Highland 52 | Goldendale 50 | League | 2.986 |
| 01/26/07 | Won | Highland 51 | Naches Valley 47 | League | 5.890 |
| 02/03/07 | Won | Highland 55 | Zillah 35 | League | 9.426 |
| 02/08/07 | Won | Highland 56 | Granger 52 | League | 9.306 |
| 02/10/07 | Lost | Highland 48 | Warden 57 | Playoff | 4.091 |
| 11/30/07 | Won | Highland 61 | Kiona-Benton 44 | Non-league | 5.479 |
| 12/07/07 | Won | Highland 61 | Columbia (Burbank) 56 | Non-league | 13.979 |
| 12/18/07 | Lost | Highland 42 | Cle Elum-Roslyn 68 | League | 2.966 |
| 01/11/08 | Won | Highland 46 | Zillah 45 | League | 9.300 |
| 01/12/08 | Won | Highland 68 | Mabton 67 | League | 9.540 |
| 01/19/08 | Lost | Highland 42 | Cle Elum-Roslyn 62 | League | 2.966 |
| 01/30/08 | Won | Highland 55 | Goldendale 50 | League | 9.678 |
| 02/01/08 | Won | Highland 54 | Mabton 45 | League | 9.540 |
| 01/16/09 | Won | Highland 50 | Mabton 49 | League | 1.637 |
| 01/24/09 | Lost | Highland 45 | Zillah 47 | League | 3.098 |
| 02/19/09 | Won | Highland 54 | Connell 49 | Playoff | 3.609 |
| 12/05/09 | Lost | Highland 56 | Wahluke 57 | Non-league | 4.917 |
| 01/25/11 | Lost | Highland 46 | La Salle 49 | League | 0.395 |
| 12/06/11 | Lost | Highland 56 | Kittitas 65 | Non-league | 6.733 |
| 12/10/11 | Won | Highland 45 | River View 40 | Non-league | 0.773 |
| 11/30/12 | Won | Highland 56 | Toppenish 47 | Non-league | 2.192 |
| 12/04/12 | Lost | Highland 64 | Selah 65 | Non-league | 3.342 |
| 01/04/13 | Lost | Highland 44 | River View 57 | Non-league | 3.820 |
| 01/05/13 | Won | Highland 61 | La Salle 56 | League | 2.315 |
| 01/25/13 | Won | Highland 62 | La Salle 50 | League | 2.315 |
| 02/09/13 | Lost | Highland 37 | Columbia (Burbank) 46 | Playoff | 5.014 |
| 12/10/13 | Lost | Highland 43 | Selah 44 | Non-league | 4.828 |
| 01/17/14 | Won | Highland 73 | Granger 67 | League | 5.474 |
| 01/31/14 | Won | Highland 49 | La Salle 46 | League | 12.513 |
| 02/01/14 | Lost | Highland 67 | Mabton 72 | League | 2.345 |
| 02/15/14 | Won | Highland 53 | River View 49 | Playoff | 2.213 |
| 12/09/14 | Won | Highland 44 | River View 42 | Non-league | 1.752 |
| 12/12/14 | Won | Highland 58 | Royal 48 | Non-league | 7.710 |
| 12/15/15 | Won | Highland 64 | White Swan 49 | Non-league | 1.464 |
| 12/28/15 | Won | Highland 48 | Royal 36 | Non-league | 6.757 |
| 01/05/16 | Lost | Highland 35 | Goldendale 44 | League | 1.134 |
| 01/09/16 | Won | Highland 57 | Cle Elum-Roslyn 54 | League | 11.414 |
| 01/15/16 | Won | Highland 62 | Columbia (Burbank) 55 | Non-league | 8.102 |
| 01/19/16 | Won | Highland 69 | Wahluke 58 | Non-league | 3.627 |
| 12/12/17 | Won | Highland 60 | Goldendale 56 | League | 7.960 |
| 01/09/18 | Won | Highland 55 | La Salle 51 | League | 25.740 |