43 Wins, 47 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/05/97 | Won | Skyline 51 | Sammamish 49 | Non-league | 4.640 |
| 12/19/97 | Lost | Skyline 62 | Bellevue 70 | League | 3.197 |
| 01/07/98 | Won | Skyline 30 | Interlake 26 | League | 7.440 |
| 01/28/98 | Won | Skyline 49 | Newport (Bellevue) 47 | League | 1.698 |
| 12/02/98 | Won | Skyline 75 | Eastlake 68 | Non-league | 5.940 |
| 12/08/98 | Lost | Skyline 56 | Lindbergh 62 | Non-league | 4.422 |
| 01/15/99 | Won | Skyline 53 | Mercer Island 47 | League | 9.448 |
| 02/10/99 | Won | Skyline 46 | Mount Si 37 | League | 0.037 |
| 12/03/99 | Lost | Skyline 57 | Eastlake 60 | Non-league | 7.115 |
| 12/11/99 | Won | Skyline 52 | Battle Ground 49 | Non-league | 5.358 |
| 01/26/00 | Lost | Skyline 32 | Mount Si 38 | League | 11.826 |
| 02/12/00 | Won | Skyline 57 | Mercer Island 45 | Playoff | 0.095 |
| 12/13/00 | Lost | Skyline 41 | Cedarcrest 44 | League | 11.789 |
| 12/28/00 | Won | Skyline 56 | Garfield 44 | Non-league | 7.166 |
| 12/30/00 | Lost | Skyline 37 | Mercer Island 47 | Non-league | 4.409 |
| 01/03/01 | Lost | Skyline 51 | Mercer Island 59 | League | 4.409 |
| 01/10/01 | Lost | Skyline 42 | Sammamish 55 | League | 1.225 |
| 01/26/01 | Won | Skyline 58 | Issaquah 47 | League | 6.315 |
| 12/28/01 | Lost | Skyline 37 | Eastlake 39 | Non-league | 10.734 |
| 01/18/02 | Lost | Skyline 49 | Mercer Island 59 | League | 10.984 |
| 02/01/02 | Lost | Skyline 30 | Newport (Bellevue) 40 | League | 4.782 |
| 02/09/02 | Lost | Skyline 48 | Liberty (Issaquah) 53 | Playoff | 10.140 |
| 12/20/02 | Won | Skyline 56 | Newport (Bellevue) 44 | League | 0.503 |
| 12/30/02 | Lost | Skyline 54 | Sehome 55 | Non-league | 0.341 |
| 01/15/03 | Lost | Skyline 60 | Mount Si 61 | League | 5.507 |
| 02/18/03 | Won | Skyline 53 | Bishop Blanchet 52 | Playoff | 3.507 |
| 02/21/03 | Won | Skyline 65 | Rainier Beach 64 | Playoff | 11.587 |
| 02/25/03 | Won | Skyline 49 | Seattle Prep 47 | Playoff | 9.140 |
| 03/05/03 | Won | Skyline 50 | Ellensburg 42 | Playoff | 1.804 |
| 12/08/03 | Won | Skyline 44 | King's 43 | Non-league | 0.140 |
| 01/17/04 | Lost | Skyline 43 | Gig Harbor 48 | Non-league | 1.309 |
| 01/23/04 | Won | Skyline 52 | Bellevue 50 | League | 3.281 |
| 02/09/04 | Won | Skyline 51 | Bellevue 49 | Playoff | 3.281 |
| 12/03/04 | Lost | Skyline 45 | Newport (Bellevue) 52 | Non-league | 6.742 |
| 01/07/05 | Won | Skyline 50 | Redmond 39 | League | 9.213 |
| 01/12/05 | Lost | Skyline 40 | Roosevelt 51 | League | 5.243 |
| 12/20/05 | Lost | Skyline 58 | Liberty (Issaquah) 60 | Non-league | 13.556 |
| 01/13/06 | Lost | Skyline 46 | Ballard 54 | League | 6.380 |
| 02/03/06 | Lost | Skyline 45 | Bothell 51 | League | 8.738 |
| 02/28/06 | Won | Skyline 47 | Inglemoor 43 | Playoff | 9.374 |
| 12/01/06 | Lost | Skyline 58 | Mount Si 65 | League | 14.605 |
| 01/20/07 | Lost | Skyline 46 | Issaquah 61 | League | 4.002 |
| 03/10/07 | Lost | Skyline 45 | Seattle Prep 59 | Playoff | 1.278 |
| 01/25/08 | Lost | Skyline 51 | Interlake 53 | League | 11.174 |
| 02/12/08 | Lost | Skyline 41 | Mercer Island 61 | Playoff | 2.576 |
| 02/26/08 | Lost | Skyline 32 | Nathan Hale 34 | Playoff | 4.541 |
| 12/06/08 | Lost | Skyline 53 | Meadowdale 55 | Non-league | 4.254 |
| 12/10/08 | Won | Skyline 49 | Garfield 46 | League | 4.639 |
| 01/09/09 | Won | Skyline 45 | Redmond 44 | League | 0.720 |
| 01/14/09 | Won | Skyline 49 | Roosevelt 38 | League | 2.387 |
| 01/28/09 | Lost | Skyline 43 | Inglemoor 58 | League | 3.686 |
| 02/04/09 | Lost | Skyline 49 | Woodinville 56 | League | 3.294 |
| 02/06/09 | Won | Skyline 59 | Newport (Bellevue) 47 | League | 3.237 |
| 02/11/09 | Won | Skyline 58 | Redmond 50 | League | 0.720 |
| 02/13/09 | Won | Skyline 50 | Issaquah 48 | League | 7.675 |
| 01/08/10 | Lost | Skyline 39 | Redmond 46 | League | 4.479 |
| 01/29/10 | Won | Skyline 49 | Eastlake 47 | League | 2.896 |
| 02/05/10 | Won | Skyline 57 | Newport (Bellevue) 22 | League | 4.109 |
| 02/10/10 | Lost | Skyline 33 | Redmond 47 | League | 4.479 |
| 02/20/10 | Lost | Skyline 40 | Lake Washington 43 | Playoff | 9.226 |
| 12/08/10 | Lost | Skyline 47 | Roosevelt 49 | League | 9.855 |
| 02/12/11 | Won | Skyline 58 | Issaquah 55 | Playoff | 3.714 |
| 02/25/11 | Lost | Skyline 54 | South Kitsap 64 | Playoff | 3.628 |
| 11/30/11 | Lost | Skyline 34 | Bellevue 37 | Non-league | 14.289 |
| 01/31/12 | Won | Skyline 37 | Issaquah 32 | League | 1.684 |
| 02/11/12 | Lost | Skyline 49 | Eastlake 54 | Playoff | 1.829 |
| 02/16/12 | Won | Skyline 47 | Issaquah 41 | Playoff | 1.684 |
| 12/19/12 | Won | Skyline 56 | Woodinville 53 | League | 0.618 |
| 01/09/13 | Lost | Skyline 39 | Eastlake 47 | League | 4.428 |
| 12/11/13 | Lost | Skyline 42 | Ballard 59 | League | 0.025 |
| 12/18/13 | Lost | Skyline 58 | Bothell 61 | League | 1.924 |
| 02/01/14 | Lost | Skyline 40 | Roosevelt 48 | League | 11.175 |
| 12/13/14 | Lost | Skyline 56 | Liberty (Issaquah) 57 | Non-league | 3.602 |
| 01/14/15 | Won | Skyline 72 | Bothell 58 | League | 6.975 |
| 01/30/15 | Won | Skyline 57 | Woodinville 44 | League | 5.354 |
| 02/12/15 | Lost | Skyline 50 | Eastlake 59 | Playoff | 5.103 |
| 12/04/15 | Won | Skyline 69 | Inglemoor 57 | League | 5.832 |
| 12/23/15 | Lost | Skyline 49 | Jackson 55 | Non-league | 6.747 |
| 02/05/16 | Won | Skyline 59 | Issaquah 55 | League | 1.958 |
| 02/16/16 | Won | Skyline 67 | Woodinville 57 | Playoff | 9.056 |
| 01/18/17 | Won | Skyline 51 | Woodinville 46 | League | 8.557 |
| 12/15/17 | Lost | Skyline 58 | Newport (Bellevue) 68 | League | 1.031 |
| 12/29/17 | Won | Skyline 72 | University 67 | Non-league | 8.181 |
| 01/03/18 | Lost | Skyline 55 | Mount Si 58 | League | 13.784 |
| 01/05/18 | Lost | Skyline 43 | Inglemoor 59 | League | 10.126 |
| 01/13/18 | Won | Skyline 76 | Woodinville 75 | League | 14.101 |
| 01/24/18 | Lost | Skyline 40 | Newport (Bellevue) 55 | League | 1.031 |
| 11/30/18 | Won | Skyline 49 | Liberty (Issaquah) 40 | Non-league | 1.369 |
| 01/09/19 | Won | Skyline 45 | Redmond 41 | League | 2.056 |
| 01/18/19 | Won | Skyline 46 | Mount Si 34 | League | 15.580 |
45 Wins, 46 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/17/02 | Lost | Skyline 45 | Bellevue 63 | League | 6.022 |
| 01/14/03 | Lost | Skyline 68 | Mount Si 76 | League | 8.291 |
| 01/31/03 | Won | Skyline 51 | Issaquah 48 | League | 3.534 |
| 02/22/03 | Won | Skyline 69 | Cleveland 56 | Playoff | 1.172 |
| 03/07/03 | Lost | Skyline 55 | Renton 60 | Playoff | 1.798 |
| 12/11/03 | Won | Skyline 53 | Interlake 49 | League | 5.259 |
| 12/16/03 | Won | Skyline 42 | Bellevue 37 | League | 2.689 |
| 01/20/04 | Lost | Skyline 35 | Sammamish 52 | League | 0.860 |
| 02/12/04 | Lost | Skyline 44 | Mount Si 52 | Playoff | 3.110 |
| 01/14/05 | Won | Skyline 80 | Ballard 69 | League | 0.588 |
| 01/21/05 | Won | Skyline 60 | Woodinville 56 | League | 7.789 |
| 02/11/05 | Won | Skyline 59 | Bothell 45 | League | 5.091 |
| 12/13/05 | Lost | Skyline 63 | North Mason 65 | Non-league | 7.095 |
| 12/16/05 | Won | Skyline 69 | Eastlake 66 | League | 10.030 |
| 12/17/05 | Won | Skyline 60 | Newport (Bellevue) 53 | Non-league | 0.813 |
| 01/06/06 | Won | Skyline 47 | Redmond 45 | League | 8.408 |
| 01/13/06 | Won | Skyline 52 | Ballard 51 | League | 2.434 |
| 02/07/06 | Won | Skyline 66 | Lake Washington 62 | League | 13.151 |
| 12/01/06 | Lost | Skyline 54 | Mount Si 65 | League | 0.370 |
| 12/21/06 | Won | Skyline 57 | Juanita 53 | Non-league | 4.535 |
| 01/26/07 | Lost | Skyline 70 | Interlake 73 | League | 3.542 |
| 12/29/07 | Lost | Skyline 65 | Kennedy 69 | Non-league | 1.582 |
| 01/11/08 | Won | Skyline 62 | Issaquah 57 | League | 3.503 |
| 12/16/08 | Lost | Skyline 54 | Bothell 60 | League | 3.051 |
| 12/29/08 | Won | Skyline 68 | West Valley (Yakima) 63 | Non-league | 0.616 |
| 01/17/09 | Lost | Skyline 51 | Newport (Bellevue) 56 | League | 8.865 |
| 01/20/09 | Lost | Skyline 46 | Ballard 49 | League | 5.036 |
| 02/03/09 | Lost | Skyline 46 | Woodinville 55 | League | 5.118 |
| 02/10/09 | Won | Skyline 53 | Redmond 32 | League | 2.925 |
| 12/15/09 | Lost | Skyline 54 | Bothell 57 | League | 8.401 |
| 01/18/10 | Won | Skyline 48 | Garfield 40 | League | 2.022 |
| 01/26/10 | Lost | Skyline 45 | Inglemoor 49 | League | 5.992 |
| 12/14/10 | Won | Skyline 41 | Redmond 37 | League | 0.234 |
| 12/17/10 | Lost | Skyline 52 | Newport (Bellevue) 57 | League | 2.388 |
| 01/04/11 | Won | Skyline 68 | Ballard 60 | League | 0.436 |
| 01/14/11 | Lost | Skyline 50 | Eastlake 54 | League | 6.357 |
| 01/25/11 | Won | Skyline 49 | Redmond 42 | League | 0.234 |
| 02/01/11 | Lost | Skyline 56 | Issaquah 59 | League | 6.676 |
| 02/04/11 | Lost | Skyline 54 | Eastlake 59 | League | 6.357 |
| 02/08/11 | Won | Skyline 48 | Inglemoor 42 | Playoff | 0.553 |
| 02/17/11 | Lost | Skyline 46 | Newport (Bellevue) 53 | Playoff | 2.388 |
| 01/03/12 | Lost | Skyline 47 | Ballard 56 | League | 8.826 |
| 01/10/12 | Won | Skyline 51 | Garfield 49 | League | 2.675 |
| 02/07/12 | Lost | Skyline 60 | Bothell 63 | Playoff | 8.937 |
| 02/10/12 | Lost | Skyline 38 | Roosevelt 39 | Playoff | 3.702 |
| 11/28/12 | Lost | Skyline 51 | Cleveland 55 | Non-league | 16.737 |
| 12/07/12 | Lost | Skyline 39 | Roosevelt 40 | League | 1.822 |
| 01/26/13 | Lost | Skyline 41 | Roosevelt 52 | League | 1.822 |
| 12/06/13 | Won | Skyline 40 | Roosevelt 34 | League | 5.292 |
| 01/10/14 | Won | Skyline 61 | Ballard 53 | League | 4.770 |
| 01/21/14 | Lost | Skyline 48 | Inglemoor 57 | League | 0.187 |
| 01/24/14 | Lost | Skyline 54 | Newport (Bellevue) 58 | League | 0.933 |
| 02/06/14 | Lost | Skyline 67 | Newport (Bellevue) 70 | League | 0.933 |
| 12/05/14 | Lost | Skyline 62 | Inglemoor 65 | League | 3.340 |
| 12/16/14 | Won | Skyline 57 | Newport (Bellevue) 49 | League | 1.361 |
| 12/20/14 | Lost | Skyline 62 | Eastlake 66 | League | 11.593 |
| 01/09/15 | Won | Skyline 76 | Issaquah 73 | League | 14.053 |
| 01/13/15 | Won | Skyline 90 | Bothell 74 | League | 1.926 |
| 01/16/15 | Lost | Skyline 56 | Inglemoor 64 | League | 3.340 |
| 01/24/15 | Won | Skyline 64 | Bothell 61 | League | 1.926 |
| 02/12/15 | Won | Skyline 72 | Bothell 71 | Playoff | 1.926 |
| 02/19/15 | Lost | Skyline 56 | Redmond 58 | Playoff | 8.213 |
| 12/04/15 | Lost | Skyline 46 | Inglemoor 61 | League | 3.029 |
| 12/15/15 | Won | Skyline 62 | Newport (Bellevue) 57 | League | 1.118 |
| 01/19/16 | Won | Skyline 41 | Newport (Bellevue) 37 | League | 1.118 |
| 02/02/16 | Lost | Skyline 72 | Mount Si 78 | League | 3.112 |
| 02/16/16 | Won | Skyline 61 | Redmond 50 | Playoff | 2.553 |
| 11/29/16 | Won | Skyline 70 | Liberty (Issaquah) 65 | Non-league | 2.107 |
| 01/06/17 | Lost | Skyline 53 | Newport (Bellevue) 55 | League | 14.576 |
| 01/10/17 | Lost | Skyline 53 | Inglemoor 56 | League | 2.653 |
| 01/24/17 | Won | Skyline 89 | Bothell 68 | League | 3.496 |
| 01/31/17 | Lost | Skyline 53 | Mount Si 56 | League | 5.133 |
| 02/03/17 | Lost | Skyline 54 | Eastlake 63 | League | 5.572 |
| 02/18/17 | Lost | Skyline 54 | Inglemoor 56 | Playoff | 2.653 |
| 11/28/17 | Won | Skyline 62 | Liberty (Issaquah) 61 | Non-league | 8.344 |
| 12/15/17 | Lost | Skyline 55 | Newport (Bellevue) 57 | League | 6.325 |
| 01/03/18 | Won | Skyline 69 | Mount Si 67 | League | 0.814 |
| 01/09/18 | Won | Skyline 63 | Bothell 62 | League | 8.990 |
| 01/12/18 | Lost | Skyline 43 | Eastlake 51 | League | 2.462 |
| 01/19/18 | Lost | Skyline 48 | Issaquah 58 | League | 5.745 |
| 01/30/18 | Won | Skyline 57 | Mount Si 49 | League | 0.814 |
| 02/17/18 | Won | Skyline 54 | Mount Si 53 | Playoff | 0.814 |
| 11/26/18 | Lost | Skyline 65 | Juanita 68 | Non-league | 6.112 |
| 11/28/18 | Won | Skyline 51 | Bellevue 48 | Non-league | 7.338 |
| 11/30/18 | Won | Skyline 52 | Liberty (Issaquah) 48 | Non-league | 7.770 |
| 12/04/18 | Lost | Skyline 60 | North Creek 63 | League | 0.820 |
| 01/25/19 | Won | Skyline 54 | Eastlake 39 | League | 3.089 |
| 02/01/19 | Won | Skyline 59 | Woodinville 53 | Playoff | 1.479 |
| 02/02/19 | Won | Skyline 43 | Bothell 33 | Playoff | 0.434 |
| 12/30/19 | Won | Skyline 73 | Auburn 68 | Non-league | 6.252 |
| 01/09/20 | Lost | Skyline 64 | Inglemoor 69 | League | 0.970 |