36 Wins, 36 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 02/03/87 | Won | Chief Sealth 46 | Seattle Lutheran 45 | Non-league | 3.407 |
| 01/04/88 | Lost | Chief Sealth 38 | Mount Rainier 53 | Non-league | 6.343 |
| 01/27/88 | Lost | Chief Sealth 35 | Nathan Hale 43 | League | 2.620 |
| 02/15/88 | Lost | Chief Sealth 44 | Nathan Hale 48 | Playoff | 2.620 |
| 03/09/88 | Won | Chief Sealth 53 | Hanford 43 | Playoff | 12.379 |
| 03/10/88 | Won | Chief Sealth 53 | West Valley (Spokane) 51 | Playoff | 6.321 |
| 03/12/88 | Won | Chief Sealth 55 | North Kitsap 52 | Playoff | 8.548 |
| 12/22/88 | Lost | Chief Sealth 33 | Seattle Prep 36 | League | 5.435 |
| 12/28/88 | Won | Chief Sealth 52 | Garfield 50 | Non-league | 23.207 |
| 02/16/89 | Lost | Chief Sealth 49 | West Seattle 51 | League | 7.483 |
| 12/15/89 | Won | Chief Sealth W | West Seattle L | League | 0.120 |
| 11/30/90 | Lost | Chief Sealth 35 | Mount Si 37 | Non-league | 10.090 |
| 12/04/90 | Lost | Chief Sealth 48 | Bellevue 63 | Non-league | 5.080 |
| 12/29/90 | Won | Chief Sealth 57 | Garfield 54 | Non-league | 10.607 |
| 01/18/91 | Won | Chief Sealth 73 | Rainier Beach 63 | League | 2.929 |
| 02/16/91 | Lost | Chief Sealth 42 | Seattle Prep 49 | Playoff | 2.889 |
| 02/26/91 | Won | Chief Sealth 44 | Lakeside (Seattle) 42 | Playoff | 5.931 |
| 02/07/92 | Won | Chief Sealth 46 | Blanchet 45 | League | 1.747 |
| 02/19/92 | Won | Chief Sealth 51 | Garfield 50 | Playoff | 9.677 |
| 03/11/92 | Won | Chief Sealth 57 | Colville 52 | Playoff | 10.725 |
| 03/12/92 | Won | Chief Sealth 55 | Sunnyside 49 | Playoff | 1.767 |
| 02/08/93 | Lost | Chief Sealth 52 | Roosevelt 57 | League | 4.724 |
| 03/05/93 | Won | Chief Sealth 50 | Blanchet 35 | Playoff | 0.353 |
| 12/20/94 | Won | Chief Sealth 66 | Inglemoor 56 | Non-league | 1.327 |
| 01/06/95 | Won | Chief Sealth 54 | Franklin 52 | League | 2.864 |
| 01/24/95 | Lost | Chief Sealth 49 | Roosevelt 53 | League | 8.943 |
| 03/10/95 | Lost | Chief Sealth 52 | Aberdeen 54 | Playoff | 0.860 |
| 03/02/96 | Won | Chief Sealth 70 | Blanchet 50 | Playoff | 6.085 |
| 12/03/96 | Lost | Chief Sealth 57 | Jefferson 61 | Non-league | 5.519 |
| 01/24/97 | Lost | Chief Sealth 63 | Roosevelt 69 | Non-league | 2.656 |
| 01/31/97 | Won | Chief Sealth 68 | Franklin 66 | Non-league | 7.561 |
| 02/21/97 | Won | Chief Sealth 53 | Blanchet 43 | Playoff | 7.669 |
| 01/09/98 | Won | Chief Sealth 58 | Seattle Prep 46 | League | 0.030 |
| 02/12/98 | Won | Chief Sealth 66 | Blanchet 52 | Playoff | 3.091 |
| 03/06/98 | Won | Chief Sealth 64 | Stanwood 57 | Playoff | 3.171 |
| 03/07/98 | Won | Chief Sealth 70 | Meadowdale 67 | Playoff | 16.062 |
| 12/01/98 | Lost | Chief Sealth 53 | Lindbergh 55 | Non-league | 3.285 |
| 12/11/98 | Lost | Chief Sealth 44 | Eastside Catholic 53 | League | 1.247 |
| 12/17/98 | Won | Chief Sealth 58 | Rainier Beach 46 | League | 10.271 |
| 02/20/99 | Won | Chief Sealth 55 | Lakeside (Seattle) 39 | Playoff | 8.947 |
| 11/29/99 | Lost | Chief Sealth L | Tyee W | Non-league | 32.389 |
| 12/11/00 | Lost | Chief Sealth 42 | Tyee 44 | Non-league | 9.263 |
| 01/23/01 | Lost | Chief Sealth 38 | Ingraham 40 | League | 15.007 |
| 11/30/01 | Won | Chief Sealth 52 | Ingraham 49 | League | 2.528 |
| 12/26/01 | Lost | Chief Sealth 42 | Interlake 52 | Non-league | 2.943 |
| 01/17/03 | Lost | Chief Sealth 70 | Holy Names 75 | League | 7.054 |
| 02/12/03 | Lost | Chief Sealth 60 | Bainbridge 63 | Playoff | 4.846 |
| 02/13/03 | Lost | Chief Sealth 55 | Eastside Catholic 61 | Playoff | 6.247 |
| 12/10/03 | Lost | Chief Sealth 42 | Bainbridge 49 | League | 7.119 |
| 12/12/03 | Lost | Chief Sealth 59 | Cleveland 66 | League | 4.761 |
| 12/17/03 | Lost | Chief Sealth 40 | Rainier Beach 51 | League | 4.492 |
| 02/11/04 | Lost | Chief Sealth 52 | Bainbridge 67 | Playoff | 7.119 |
| 02/11/05 | Lost | Chief Sealth 62 | Rainier Beach 72 | Playoff | 8.898 |
| 12/12/07 | Lost | Chief Sealth 45 | Eastside Catholic 53 | League | 6.075 |
| 01/11/08 | Won | Chief Sealth 44 | Rainier Beach 43 | League | 10.429 |
| 01/16/08 | Lost | Chief Sealth 48 | Bishop Blanchet 54 | League | 0.072 |
| 01/25/08 | Won | Chief Sealth 57 | Ingraham 53 | League | 8.831 |
| 02/05/10 | Won | Chief Sealth 42 | West Seattle 32 | League | 5.560 |
| 12/02/10 | Won | Chief Sealth 58 | Tyee 54 | Non-league | 4.232 |
| 12/16/10 | Lost | Chief Sealth 39 | West Seattle 41 | League | 12.603 |
| 01/19/11 | Lost | Chief Sealth 50 | Rainier Beach 59 | League | 0.452 |
| 02/04/11 | Lost | Chief Sealth 40 | Rainier Beach 51 | League | 0.452 |
| 12/05/12 | Won | Chief Sealth 46 | Eastside Catholic 38 | League | 9.901 |
| 12/12/12 | Lost | Chief Sealth 49 | Rainier Beach 50 | League | 8.447 |
| 01/21/15 | Lost | Chief Sealth 50 | Bainbridge 52 | League | 3.081 |
| 01/08/16 | Won | Chief Sealth 45 | Seattle Prep 42 | League | 5.356 |
| 01/22/16 | Won | Chief Sealth 45 | Lakeside (Seattle) 44 | League | 14.526 |
| 02/09/16 | Won | Chief Sealth 57 | Eastside Catholic 51 | Playoff | 5.030 |
| 12/16/16 | Won | Chief Sealth 64 | Holy Names 56 | League | 6.092 |
| 12/15/17 | Won | Chief Sealth 47 | Holy Names 32 | League | 2.202 |
| 01/12/18 | Lost | Chief Sealth 52 | Franklin 53 | League | 6.098 |
| 12/27/19 | Lost | Chief Sealth 27 | Tyee 39 | Non-league | 6.985 |
24 Wins, 29 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/10/02 | Lost | Chief Sealth 64 | Bainbridge 67 | League | 4.197 |
| 12/27/02 | Won | Chief Sealth 59 | Tahoma 38 | Non-league | 1.057 |
| 01/04/03 | Lost | Chief Sealth 49 | Ballard 52 | Non-league | 5.630 |
| 01/24/03 | Won | Chief Sealth 66 | Cleveland 57 | League | 11.553 |
| 12/06/03 | Won | Chief Sealth 60 | Ballard 56 | Non-league | 2.837 |
| 01/30/04 | Won | Chief Sealth 49 | Nathan Hale 43 | League | 6.129 |
| 12/17/04 | Lost | Chief Sealth 65 | Nathan Hale 68 | League | 0.912 |
| 01/14/05 | Won | Chief Sealth 65 | Bishop Blanchet 57 | League | 9.042 |
| 01/25/05 | Lost | Chief Sealth 48 | Ingraham 70 | League | 2.041 |
| 02/04/05 | Won | Chief Sealth 82 | Cleveland 80 | League | 10.227 |
| 01/06/06 | Lost | Chief Sealth 51 | Cleveland 69 | League | 3.003 |
| 01/13/06 | Won | Chief Sealth 65 | Bishop Blanchet 55 | League | 1.862 |
| 01/24/06 | Won | Chief Sealth 68 | Ingraham 66 | League | 1.193 |
| 12/05/06 | Won | Chief Sealth 54 | Seattle Prep 47 | League | 0.904 |
| 02/05/07 | Won | Chief Sealth 72 | Rainier Beach 63 | League | 9.710 |
| 02/06/07 | Lost | Chief Sealth 49 | Nathan Hale 56 | League | 17.079 |
| 02/23/07 | Lost | Chief Sealth 59 | Bellevue 61 | Playoff | 1.636 |
| 12/11/07 | Lost | Chief Sealth 58 | Eastside Catholic 66 | League | 5.704 |
| 01/08/08 | Lost | Chief Sealth 60 | Nathan Hale 63 | League | 4.385 |
| 01/15/08 | Won | Chief Sealth 59 | Bishop Blanchet 51 | League | 1.315 |
| 01/25/08 | Lost | Chief Sealth 62 | Ingraham 81 | League | 4.512 |
| 01/29/08 | Won | Chief Sealth 75 | West Seattle 65 | League | 5.302 |
| 02/10/09 | Won | Chief Sealth 74 | Rainier Beach 70 | League | 16.110 |
| 12/22/09 | Lost | Chief Sealth 67 | Lake Washington 73 | Non-league | 0.779 |
| 01/12/10 | Lost | Chief Sealth 47 | Seattle Prep 50 | League | 1.602 |
| 01/29/10 | Won | Chief Sealth 72 | Franklin 58 | League | 1.629 |
| 02/26/10 | Lost | Chief Sealth 39 | Sammamish 46 | Playoff | 5.477 |
| 01/14/11 | Lost | Chief Sealth 50 | Seattle Prep 57 | League | 3.052 |
| 01/17/11 | Won | Chief Sealth 60 | Bellevue 58 | Non-league | 2.156 |
| 02/17/11 | Lost | Chief Sealth 48 | Seattle Prep 51 | Playoff | 3.052 |
| 03/04/11 | Lost | Chief Sealth 46 | North Central 53 | Playoff | 6.197 |
| 12/21/11 | Won | Chief Sealth 73 | Garfield 67 | Non-league | 8.604 |
| 12/28/11 | Lost | Chief Sealth 50 | Newport (Bellevue) 55 | Non-league | 4.289 |
| 01/28/12 | Lost | Chief Sealth 49 | Bainbridge 60 | League | 5.785 |
| 02/03/12 | Lost | Chief Sealth 57 | Bainbridge 65 | League | 5.785 |
| 02/07/12 | Lost | Chief Sealth 65 | Eastside Catholic 83 | Playoff | 0.047 |
| 02/11/12 | Lost | Chief Sealth 49 | Nathan Hale 55 | Playoff | 1.654 |
| 12/04/12 | Won | Chief Sealth 56 | Eastside Catholic 54 | League | 11.222 |
| 12/18/12 | Lost | Chief Sealth 51 | West Seattle 58 | League | 7.417 |
| 01/04/13 | Lost | Chief Sealth 38 | Nathan Hale 43 | League | 4.864 |
| 02/04/13 | Lost | Chief Sealth 51 | Bainbridge 53 | Playoff | 5.596 |
| 12/19/14 | Lost | Chief Sealth 74 | Ballard 78 | League | 3.833 |
| 01/13/15 | Won | Chief Sealth 75 | Franklin 71 | League | 9.148 |
| 01/16/15 | Lost | Chief Sealth 56 | Nathan Hale 57 | League | 12.390 |
| 01/30/15 | Won | Chief Sealth 54 | Roosevelt 51 | League | 9.807 |
| 12/04/15 | Won | Chief Sealth 55 | Bishop Blanchet 50 | League | 5.211 |
| 01/29/16 | Lost | Chief Sealth 57 | Roosevelt 69 | League | 0.012 |
| 02/11/16 | Won | Chief Sealth 62 | Bishop Blanchet 61 | Playoff | 5.211 |
| 02/10/17 | Lost | Chief Sealth 59 | Ballard 61 | Playoff | 4.283 |
| 12/28/19 | Lost | Chief Sealth 50 | Peninsula 59 | Non-league | 2.113 |
| 01/03/20 | Won | Chief Sealth 61 | Lakeside (Seattle) 59 | League | 3.084 |
| 01/07/20 | Won | Chief Sealth 59 | Bainbridge 52 | League | 6.997 |
| 01/20/20 | Won | Chief Sealth 66 | Franklin 61 | League | 1.459 |