36 Wins, 35 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 01/20/89 | Won | Cleveland 39 | Nathan Hale 36 | League | 5.387 |
| 01/09/91 | Lost | Cleveland 37 | Nathan Hale 52 | League | 1.504 |
| 01/23/91 | Lost | Cleveland 43 | Holy Names 46 | League | 15.535 |
| 02/06/91 | Lost | Cleveland 40 | Ballard 49 | League | 5.717 |
| 12/01/92 | Lost | Cleveland 33 | Northwest 37 | Non-league | 5.358 |
| 12/29/95 | Won | Cleveland 53 | Mount Rainier 50 | Non-league | 6.612 |
| 01/03/96 | Won | Cleveland 40 | Rainier Beach 36 | League | 2.426 |
| 01/27/96 | Won | Cleveland 36 | Washington 35 | Non-league | 16.694 |
| 01/03/97 | Won | Cleveland 48 | Sultan 46 | Non-league | 3.334 |
| 01/21/97 | Lost | Cleveland 50 | Clover Park 52 | Non-league | 1.451 |
| 12/01/98 | Won | Cleveland 40 | Bush 18 | Non-league | 0.337 |
| 02/26/99 | Won | Cleveland 63 | Klahowya 59 | Playoff | 2.532 |
| 11/30/00 | Lost | Cleveland 44 | Hudson's Bay 57 | Non-league | 8.678 |
| 01/09/02 | Won | Cleveland 63 | Bainbridge 56 | League | 5.230 |
| 01/15/03 | Lost | Cleveland 59 | Eastside Catholic 61 | League | 7.585 |
| 01/17/03 | Won | Cleveland 59 | Bishop Blanchet 51 | League | 4.272 |
| 12/08/03 | Lost | Cleveland 71 | Lincoln 76 | Non-league | 2.720 |
| 12/12/03 | Won | Cleveland 66 | Chief Sealth 59 | League | 4.761 |
| 02/06/04 | Won | Cleveland 71 | Rainier Beach 64 | League | 0.269 |
| 02/26/04 | Lost | Cleveland 52 | Bainbridge 57 | Playoff | 2.358 |
| 12/08/04 | Lost | Cleveland 38 | Eastside Catholic 39 | League | 13.338 |
| 12/17/04 | Lost | Cleveland 38 | Ingraham 46 | League | 1.782 |
| 01/14/05 | Won | Cleveland 48 | Holy Names 37 | League | 12.015 |
| 01/28/05 | Lost | Cleveland 51 | Ingraham 58 | League | 1.782 |
| 02/07/05 | Lost | Cleveland 31 | Lakeside (Seattle) 44 | Playoff | 2.362 |
| 12/06/06 | Lost | Cleveland 41 | Bishop Blanchet 43 | League | 1.072 |
| 12/28/06 | Won | Cleveland 51 | Shelton 50 | Non-league | 2.304 |
| 01/26/07 | Lost | Cleveland 46 | West Seattle 51 | League | 0.661 |
| 02/06/07 | Won | Cleveland 45 | Ingraham 43 | League | 9.450 |
| 12/07/07 | Lost | Cleveland 39 | Bishop Blanchet 53 | League | 3.303 |
| 01/11/08 | Won | Cleveland 51 | Nathan Hale 40 | League | 4.141 |
| 02/02/08 | Won | Cleveland 60 | Rainier Beach 53 | League | 7.198 |
| 02/11/08 | Lost | Cleveland 54 | Bishop Blanchet 59 | Playoff | 3.303 |
| 12/10/08 | Won | Cleveland 56 | Seattle Prep 53 | League | 1.028 |
| 01/07/09 | Lost | Cleveland 67 | Nathan Hale 68 | League | 0.770 |
| 02/18/09 | Lost | Cleveland 46 | Nathan Hale 59 | Playoff | 0.770 |
| 02/24/09 | Won | Cleveland 51 | Bainbridge 46 | Playoff | 3.048 |
| 01/06/10 | Lost | Cleveland 48 | Nathan Hale 57 | League | 9.770 |
| 01/15/10 | Lost | Cleveland 44 | Franklin 52 | League | 8.232 |
| 02/17/10 | Lost | Cleveland 50 | Seattle Prep 54 | Playoff | 4.146 |
| 03/10/10 | Won | Cleveland 68 | White River 57 | Playoff | 0.757 |
| 03/12/10 | Won | Cleveland 57 | Mercer Island 55 | Playoff | 8.706 |
| 03/13/10 | Won | Cleveland 47 | Holy Names 44 | Playoff | 13.129 |
| 02/15/11 | Lost | Cleveland 62 | Mercer Island 65 | Playoff | 11.303 |
| 02/25/11 | Lost | Cleveland 61 | Eastmont 62 | Playoff | 12.687 |
| 12/16/11 | Won | Cleveland 46 | Franklin 40 | League | 1.982 |
| 12/29/11 | Lost | Cleveland 53 | Seattle Prep 59 | Non-league | 3.156 |
| 02/16/12 | Lost | Cleveland 33 | Lakeside (Seattle) 34 | Playoff | 8.741 |
| 02/18/12 | Lost | Cleveland 38 | Seattle Prep 55 | Playoff | 3.156 |
| 02/25/12 | Won | Cleveland 46 | Wilson 41 | Playoff | 9.229 |
| 03/03/12 | Won | Cleveland 50 | University 40 | Playoff | 4.100 |
| 01/21/13 | Won | Cleveland 60 | Wilson 53 | Non-league | 0.927 |
| 01/01/14 | Won | Cleveland 59 | Lynnwood 49 | Non-league | 2.097 |
| 12/12/14 | Lost | Cleveland 39 | Lakeside (Seattle) 41 | League | 11.292 |
| 02/21/15 | Won | Cleveland 57 | West Seattle 54 | Playoff | 2.478 |
| 02/28/15 | Won | Cleveland 62 | Glacier Peak 52 | Playoff | 6.268 |
| 03/06/15 | Won | Cleveland 55 | Bishop Blanchet 48 | Playoff | 2.536 |
| 12/14/15 | Won | Cleveland 58 | Lincoln 49 | Non-league | 8.551 |
| 01/27/16 | Won | Cleveland 68 | Garfield 42 | League | 4.412 |
| 01/30/16 | Lost | Cleveland 30 | Seattle Prep 43 | League | 4.558 |
| 12/07/16 | Lost | Cleveland 46 | Lakeside (Seattle) 49 | League | 2.321 |
| 01/13/17 | Lost | Cleveland 54 | Holy Names 63 | League | 7.279 |
| 02/11/17 | Won | Cleveland 61 | Juanita 57 | Playoff | 5.102 |
| 01/10/18 | Lost | Cleveland 56 | Ballard 68 | League | 5.603 |
| 02/02/18 | Won | Cleveland 45 | Rainier Beach 41 | League | 2.230 |
| 02/07/18 | Won | Cleveland 63 | West Seattle 60 | Playoff | 10.201 |
| 02/09/18 | Won | Cleveland 53 | Seattle Prep 50 | Playoff | 5.737 |
| 02/15/18 | Won | Cleveland 45 | Garfield 41 | Playoff | 13.002 |
| 02/24/18 | Lost | Cleveland 36 | Shorecrest 43 | Playoff | 3.344 |
| 12/15/18 | Lost | Cleveland 36 | Federal Way 40 | Non-league | 8.728 |
| 12/04/19 | Lost | Cleveland 51 | Stadium 63 | Non-league | 1.303 |
32 Wins, 39 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/06/02 | Won | Cleveland 72 | O'Dea 67 | League | 3.379 |
| 01/10/03 | Won | Cleveland 65 | Rainier Beach 60 | League | 23.367 |
| 01/21/03 | Lost | Cleveland 51 | Bainbridge 53 | League | 15.750 |
| 01/24/03 | Lost | Cleveland 57 | Chief Sealth 66 | League | 11.553 |
| 01/31/03 | Lost | Cleveland 58 | Ingraham 60 | League | 10.255 |
| 02/12/03 | Won | Cleveland 61 | O'Dea 50 | Playoff | 3.379 |
| 02/22/03 | Lost | Cleveland 56 | Skyline 69 | Playoff | 1.172 |
| 02/27/03 | Lost | Cleveland 45 | Newport (Bellevue) 58 | Playoff | 0.392 |
| 02/26/04 | Won | Cleveland 80 | Seattle Prep 71 | Playoff | 1.422 |
| 03/03/04 | Lost | Cleveland 74 | Timberline 76 | Playoff | 3.861 |
| 11/30/04 | Lost | Cleveland 72 | Bainbridge 76 | League | 2.249 |
| 01/25/05 | Lost | Cleveland 74 | West Seattle 76 | League | 3.166 |
| 02/04/05 | Lost | Cleveland 80 | Chief Sealth 82 | League | 10.227 |
| 02/12/05 | Lost | Cleveland 47 | Bishop Blanchet 54 | Playoff | 1.185 |
| 02/22/05 | Lost | Cleveland 48 | West Seattle 57 | Playoff | 3.166 |
| 11/29/05 | Won | Cleveland 85 | Bainbridge 84 | League | 13.960 |
| 12/06/05 | Lost | Cleveland 53 | Eastside Catholic 64 | League | 4.762 |
| 12/09/05 | Won | Cleveland 65 | Rainier Beach 60 | League | 19.690 |
| 12/15/05 | Won | Cleveland 69 | Ingraham 62 | League | 4.196 |
| 12/17/05 | Lost | Cleveland 63 | Issaquah 64 | Non-league | 2.452 |
| 12/22/05 | Lost | Cleveland 49 | Stadium 65 | Non-league | 4.643 |
| 01/06/06 | Won | Cleveland 69 | Chief Sealth 51 | League | 3.003 |
| 01/24/06 | Lost | Cleveland 54 | West Seattle 68 | League | 6.058 |
| 02/11/06 | Won | Cleveland 62 | Ingraham 48 | Playoff | 4.196 |
| 01/19/07 | Won | Cleveland 58 | Seattle Prep 54 | League | 8.284 |
| 02/08/07 | Lost | Cleveland 51 | Nathan Hale 59 | League | 9.698 |
| 12/05/07 | Lost | Cleveland 69 | Mount Rainier 75 | Non-league | 3.458 |
| 01/15/08 | Lost | Cleveland 52 | Bainbridge 70 | League | 5.877 |
| 02/14/08 | Lost | Cleveland 48 | O'Dea 54 | Playoff | 2.730 |
| 02/28/08 | Lost | Cleveland 52 | West Seattle 56 | Playoff | 9.668 |
| 01/09/09 | Lost | Cleveland 31 | Lakeside (Seattle) 36 | League | 10.689 |
| 01/20/09 | Won | Cleveland 52 | Bishop Blanchet 43 | League | 5.134 |
| 01/23/09 | Lost | Cleveland 48 | West Seattle 51 | League | 5.530 |
| 02/03/09 | Lost | Cleveland 55 | Ingraham 64 | League | 1.696 |
| 02/10/09 | Lost | Cleveland 63 | Ingraham 65 | League | 1.696 |
| 02/16/09 | Won | Cleveland 63 | Bishop Blanchet 58 | Playoff | 5.134 |
| 02/24/09 | Won | Cleveland 61 | Bainbridge 51 | Playoff | 6.402 |
| 12/18/09 | Lost | Cleveland 61 | Eastside Catholic 66 | League | 1.553 |
| 02/09/10 | Lost | Cleveland 62 | Ingraham 73 | League | 2.786 |
| 11/30/10 | Lost | Cleveland 45 | Highline 50 | Non-league | 4.052 |
| 01/14/11 | Won | Cleveland 61 | Bainbridge 51 | League | 6.916 |
| 01/25/11 | Won | Cleveland 65 | Ingraham 55 | League | 2.048 |
| 01/29/11 | Won | Cleveland 84 | Ingraham 75 | League | 2.048 |
| 02/03/12 | Won | Cleveland 65 | Ingraham 61 | League | 8.276 |
| 11/28/12 | Won | Cleveland 55 | Skyline 51 | Non-league | 16.737 |
| 12/07/12 | Lost | Cleveland 51 | Ingraham 57 | League | 9.422 |
| 01/08/13 | Lost | Cleveland 58 | Ingraham 62 | League | 9.422 |
| 12/07/13 | Lost | Cleveland 46 | Seattle Academy 54 | Non-league | 2.944 |
| 12/26/13 | Won | Cleveland 81 | Foss 79 | Non-league | 5.805 |
| 01/21/14 | Won | Cleveland 69 | West Seattle 46 | League | 0.642 |
| 01/24/14 | Won | Cleveland 63 | Nathan Hale 56 | League | 0.152 |
| 12/20/14 | Won | Cleveland 67 | Davis 59 | Non-league | 1.147 |
| 01/09/15 | Lost | Cleveland 58 | Bainbridge 64 | League | 1.650 |
| 01/13/15 | Lost | Cleveland 42 | West Seattle 47 | League | 0.083 |
| 01/20/15 | Lost | Cleveland 52 | Ballard 54 | League | 11.491 |
| 02/10/15 | Lost | Cleveland 60 | Bainbridge 63 | Playoff | 1.650 |
| 12/19/15 | Lost | Cleveland 56 | Davis 69 | Non-league | 6.798 |
| 01/05/16 | Lost | Cleveland 70 | Eastside Catholic 75 | League | 5.751 |
| 01/18/16 | Won | Cleveland 68 | O'Dea 59 | League | 1.235 |
| 02/20/16 | Won | Cleveland 62 | O'Dea 59 | Playoff | 1.235 |
| 01/16/17 | Won | Cleveland 70 | Franklin 68 | League | 2.248 |
| 01/17/17 | Lost | Cleveland 51 | Eastside Catholic 52 | League | 0.155 |
| 02/10/17 | Won | Cleveland 66 | Franklin 65 | Playoff | 2.248 |
| 01/26/18 | Won | Cleveland 72 | Franklin 69 | League | 2.040 |
| 02/05/18 | Won | Cleveland 58 | Seattle Prep 56 | Playoff | 4.610 |
| 11/27/18 | Won | Cleveland 54 | Foster 51 | Non-league | 11.071 |
| 11/30/18 | Won | Cleveland 66 | Garfield 65 | League | 21.547 |
| 12/21/18 | Won | Cleveland 67 | Lakeside (Seattle) 55 | League | 8.239 |
| 01/25/19 | Won | Cleveland 63 | Ballard 62 | League | 1.184 |
| 01/04/20 | Lost | Cleveland 57 | Lakeside (Seattle) 59 | League | 0.071 |
| 02/10/20 | Lost | Cleveland 61 | Lakeside (Seattle) 67 | Playoff | 0.071 |