59 Wins, 52 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 02/03/87 | Won | Roosevelt 55 | Blanchet 53 | League | 7.451 |
| 01/08/88 | Won | Roosevelt 52 | Blanchet 50 | League | 3.511 |
| 02/16/89 | Won | Roosevelt 54 | Ballard 34 | League | 5.931 |
| 12/08/89 | Lost | Roosevelt 46 | Marysville-Pilchuck 53 | Non-league | 0.757 |
| 12/13/89 | Won | Roosevelt 45 | Franklin 41 | Non-league | 15.445 |
| 01/19/90 | Won | Roosevelt 31 | Franklin 29 | League | 15.445 |
| 01/23/90 | Lost | Roosevelt L | Ingraham W | League | 11.724 |
| 02/14/90 | Lost | Roosevelt 49 | Ingraham 55 | Playoff | 11.724 |
| 12/06/91 | Won | Roosevelt 45 | Shorecrest 43 | Non-league | 6.354 |
| 12/17/91 | Won | Roosevelt 46 | Rainier Beach 42 | League | 2.365 |
| 12/19/91 | Won | Roosevelt 43 | Seattle Prep 39 | League | 13.779 |
| 02/22/92 | Won | Roosevelt 52 | Rainier Beach 50 | Playoff | 2.365 |
| 12/09/92 | Lost | Roosevelt 42 | Mariner 49 | Non-league | 1.087 |
| 01/25/93 | Lost | Roosevelt 38 | Franklin 51 | League | 3.159 |
| 02/08/93 | Won | Roosevelt 57 | Chief Sealth 52 | League | 4.724 |
| 02/19/93 | Won | Roosevelt 41 | Blanchet 40 | Playoff | 5.077 |
| 03/06/93 | Won | Roosevelt 44 | Blanchet 40 | Playoff | 5.077 |
| 12/21/93 | Won | Roosevelt 55 | Blaine 53 | Non-league | 3.716 |
| 02/26/94 | Lost | Roosevelt 39 | Blanchet 47 | Playoff | 1.621 |
| 12/22/94 | Lost | Roosevelt 49 | Blaine 53 | Non-league | 6.048 |
| 01/24/95 | Won | Roosevelt 53 | Chief Sealth 49 | League | 8.943 |
| 02/23/95 | Lost | Roosevelt 47 | Kennedy 53 | Playoff | 4.835 |
| 02/25/95 | Lost | Roosevelt 59 | Mount Si 61 | Playoff | 0.281 |
| Lost | Roosevelt L | Garfield W | League | 0.312 | |
| 01/10/97 | Lost | Roosevelt 47 | Holy Names 66 | Non-league | 5.549 |
| 01/24/97 | Won | Roosevelt 69 | Chief Sealth 63 | Non-league | 2.656 |
| 02/12/97 | Won | Roosevelt 52 | Blanchet 48 | Non-league | 10.325 |
| 01/09/98 | Lost | Roosevelt 54 | Inglemoor 66 | League | 0.194 |
| 01/16/98 | Won | Roosevelt 63 | Redmond 60 | League | 0.572 |
| 01/21/98 | Lost | Roosevelt 56 | Lake Washington 61 | League | 7.232 |
| 02/11/98 | Won | Roosevelt 62 | Redmond 48 | League | 0.572 |
| 02/21/98 | Won | Roosevelt 60 | Bothell 43 | Playoff | 2.809 |
| 02/27/98 | Won | Roosevelt 58 | Redmond 48 | Playoff | 0.572 |
| 02/28/98 | Lost | Roosevelt 36 | Inglemoor 52 | Playoff | 0.194 |
| 03/04/98 | Lost | Roosevelt 46 | Snohomish 50 | Playoff | 4.916 |
| 01/20/99 | Won | Roosevelt 70 | Lake Washington 68 | League | 1.798 |
| 03/05/99 | Lost | Roosevelt 51 | Cascade (Everett) 65 | Playoff | 4.098 |
| 12/02/00 | Lost | Roosevelt 45 | Port Angeles 61 | Non-league | 0.798 |
| 01/05/01 | Lost | Roosevelt 41 | Lake Washington 43 | League | 9.584 |
| 01/17/01 | Lost | Roosevelt 51 | Redmond 52 | League | 1.445 |
| 03/09/01 | Lost | Roosevelt 39 | Enumclaw 56 | Playoff | 0.736 |
| 01/04/02 | Lost | Roosevelt 51 | Garfield 52 | League | 13.629 |
| 03/06/02 | Lost | Roosevelt 42 | Kentlake 48 | Playoff | 17.695 |
| 12/20/02 | Won | Roosevelt 48 | Lake Washington 47 | League | 6.384 |
| 12/27/02 | Won | Roosevelt 49 | Port Angeles 45 | Non-league | 0.334 |
| 12/02/03 | Lost | Roosevelt 38 | Issaquah 49 | Non-league | 15.121 |
| 02/04/04 | Won | Roosevelt 78 | Redmond 61 | League | 2.920 |
| 02/28/04 | Won | Roosevelt 49 | Redmond 43 | Playoff | 2.920 |
| 03/06/04 | Won | Roosevelt 42 | Redmond 41 | Playoff | 2.920 |
| 03/11/04 | Won | Roosevelt 59 | Lewis and Clark 50 | Playoff | 3.853 |
| 03/12/04 | Won | Roosevelt 58 | Snohomish 54 | Playoff | 4.150 |
| 03/13/04 | Won | Roosevelt 55 | Garfield 52 | Playoff | 8.997 |
| 11/30/04 | Won | Roosevelt 50 | Issaquah 41 | Non-league | 7.630 |
| 12/20/04 | Lost | Roosevelt 42 | Newport (Bellevue) 57 | Non-league | 1.499 |
| 01/07/05 | Lost | Roosevelt 57 | Franklin 59 | League | 3.300 |
| 01/12/05 | Won | Roosevelt 51 | Skyline 40 | League | 5.243 |
| 02/16/05 | Lost | Roosevelt 51 | Ballard 53 | League | 9.114 |
| 02/23/05 | Won | Roosevelt 44 | Inglemoor 40 | Playoff | 6.957 |
| 12/23/05 | Lost | Roosevelt 66 | Newport (Bellevue) 69 | Non-league | 10.386 |
| 02/08/06 | Won | Roosevelt 59 | Garfield 57 | League | 9.857 |
| 02/22/06 | Won | Roosevelt 43 | Inglemoor 41 | Playoff | 2.577 |
| 03/04/06 | Won | Roosevelt 56 | Garfield 55 | Playoff | 9.857 |
| 03/09/06 | Lost | Roosevelt 49 | Gig Harbor 63 | Playoff | 4.307 |
| 12/22/06 | Won | Roosevelt 71 | Prairie 64 | Non-league | 1.346 |
| 12/08/07 | Won | Roosevelt 53 | Kentwood 48 | Non-league | 5.717 |
| 01/23/08 | Lost | Roosevelt 38 | Franklin 41 | League | 7.587 |
| 02/06/08 | Won | Roosevelt 44 | Ballard 31 | League | 1.218 |
| 02/16/08 | Lost | Roosevelt 37 | Inglemoor 54 | Playoff | 1.425 |
| 02/19/08 | Lost | Roosevelt 31 | Redmond 51 | Playoff | 2.077 |
| 12/15/08 | Won | Roosevelt 61 | Newport (Bellevue) 55 | League | 0.850 |
| 01/07/09 | Won | Roosevelt 55 | Issaquah 45 | League | 5.288 |
| 01/14/09 | Lost | Roosevelt 38 | Skyline 49 | League | 2.387 |
| 01/24/09 | Lost | Roosevelt 46 | Inglemoor 52 | League | 6.074 |
| 01/28/09 | Lost | Roosevelt 44 | Redmond 49 | League | 1.667 |
| 01/08/10 | Lost | Roosevelt 43 | Lake Washington 45 | League | 7.247 |
| 02/03/10 | Won | Roosevelt 40 | Garfield 28 | League | 8.912 |
| 12/08/10 | Won | Roosevelt 49 | Skyline 47 | League | 9.855 |
| 01/05/11 | Lost | Roosevelt 47 | Redmond 58 | League | 9.052 |
| 01/07/11 | Won | Roosevelt 52 | Woodinville 40 | League | 17.988 |
| 01/28/11 | Won | Roosevelt 56 | Inglemoor 54 | League | 7.501 |
| 12/01/11 | Won | Roosevelt 58 | Franklin 54 | Non-league | 17.750 |
| 12/09/11 | Won | Roosevelt 67 | Garfield 59 | League | 8.407 |
| 12/20/11 | Won | Roosevelt 45 | Newport (Bellevue) 42 | League | 5.017 |
| 01/04/12 | Won | Roosevelt 45 | Redmond 41 | League | 0.854 |
| 01/21/12 | Won | Roosevelt 46 | Ballard 37 | League | 2.506 |
| 01/04/13 | Won | Roosevelt 41 | Issaquah 40 | League | 21.753 |
| 12/20/13 | Lost | Roosevelt 39 | Garfield 42 | League | 0.863 |
| 12/28/13 | Lost | Roosevelt 45 | Meadowdale 52 | Non-league | 0.083 |
| 02/01/14 | Won | Roosevelt 48 | Skyline 40 | League | 11.175 |
| 02/10/15 | Lost | Roosevelt 45 | Bainbridge 47 | Playoff | 10.358 |
| 12/29/15 | Lost | Roosevelt 35 | Tahoma 51 | Non-league | 3.654 |
| 01/06/16 | Won | Roosevelt 37 | Rainier Beach 32 | League | 2.663 |
| 01/15/16 | Won | Roosevelt 59 | Garfield 53 | League | 0.021 |
| 01/20/16 | Lost | Roosevelt 39 | Seattle Prep 40 | League | 8.949 |
| 02/11/16 | Won | Roosevelt 44 | Lakeside (Seattle) 35 | Playoff | 0.221 |
| 11/29/16 | Lost | Roosevelt 36 | Olympia 40 | Non-league | 1.779 |
| 12/09/16 | Lost | Roosevelt 50 | Holy Names 51 | League | 6.801 |
| 01/11/17 | Won | Roosevelt 49 | Seattle Prep 45 | League | 8.568 |
| 02/10/17 | Lost | Roosevelt 42 | Lakeside (Seattle) 48 | Playoff | 1.843 |
| 12/04/17 | Lost | Roosevelt 46 | Lakes 49 | Non-league | 7.196 |
| 01/12/18 | Lost | Roosevelt 38 | Bainbridge 47 | League | 2.644 |
| 11/30/18 | Lost | Roosevelt 42 | Lakeside (Seattle) 45 | League | 5.506 |
| 12/01/18 | Won | Roosevelt 63 | Bethel 48 | Non-league | 1.398 |
| 02/15/19 | Lost | Roosevelt 45 | Lake Washington 47 | Playoff | 2.511 |
| 02/27/19 | Won | Roosevelt 60 | Peninsula 56 | Playoff | 4.081 |
| 12/07/19 | Won | Roosevelt 35 | Prairie 31 | Non-league | 12.197 |
| 12/13/19 | Won | Roosevelt 49 | Bainbridge 41 | League | 0.171 |
| 01/18/20 | Lost | Roosevelt 32 | Monroe 37 | Non-league | 5.089 |
| 01/31/20 | Lost | Roosevelt 32 | Holy Names 50 | League | 0.674 |
| 02/07/20 | Lost | Roosevelt 23 | Ballard 38 | League | 5.756 |
| 02/13/20 | Lost | Roosevelt 38 | Rainier Beach 50 | Playoff | 2.649 |
32 Wins, 52 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/12/02 | Won | Roosevelt 81 | Franklin 75 | League | 23.915 |
| 02/07/03 | Lost | Roosevelt 49 | Bothell 57 | League | 0.038 |
| 02/28/03 | Lost | Roosevelt 87 | Lake Washington 89 | Playoff | 7.656 |
| 12/09/03 | Lost | Roosevelt 54 | Newport (Bellevue) 59 | Non-league | 8.142 |
| 12/19/03 | Won | Roosevelt 57 | Lake Washington 52 | League | 0.737 |
| 01/20/04 | Lost | Roosevelt 69 | Woodinville 81 | League | 1.195 |
| 01/24/04 | Lost | Roosevelt 47 | Garfield 49 | League | 0.386 |
| 01/30/04 | Won | Roosevelt 64 | Lake Washington 61 | League | 0.737 |
| 02/06/04 | Won | Roosevelt 62 | Bothell 49 | League | 2.573 |
| 02/27/04 | Lost | Roosevelt 46 | Woodinville 48 | Playoff | 1.195 |
| 12/11/04 | Lost | Roosevelt 55 | Kent-Meridian 67 | Non-league | 2.411 |
| 02/08/05 | Lost | Roosevelt 53 | Garfield 56 | League | 15.156 |
| 02/25/05 | Lost | Roosevelt 67 | Franklin 77 | Playoff | 0.423 |
| 03/11/05 | Lost | Roosevelt 51 | Prairie 55 | Playoff | 3.646 |
| 12/10/05 | Won | Roosevelt 62 | Ingraham 58 | Non-league | 1.288 |
| 12/16/05 | Lost | Roosevelt 45 | Ballard 51 | League | 3.450 |
| 12/28/05 | Lost | Roosevelt 48 | Wilson 55 | Non-league | 7.728 |
| 12/30/05 | Lost | Roosevelt 53 | Lincoln 55 | Non-league | 2.855 |
| 01/13/06 | Won | Roosevelt 42 | Eastlake 35 | League | 4.145 |
| 01/24/06 | Won | Roosevelt 50 | Redmond 49 | League | 2.524 |
| 01/27/06 | Lost | Roosevelt 34 | Bothell 37 | League | 2.006 |
| 01/31/06 | Lost | Roosevelt 51 | Woodinville 54 | League | 1.148 |
| 12/08/06 | Lost | Roosevelt 50 | Redmond 62 | League | 3.468 |
| 12/29/06 | Lost | Roosevelt 42 | Bethel 43 | Non-league | 5.150 |
| 01/09/07 | Won | Roosevelt 69 | Inglemoor 58 | League | 0.653 |
| 01/27/07 | Lost | Roosevelt 46 | Ballard 51 | League | 12.272 |
| 02/03/07 | Lost | Roosevelt 44 | Eastlake 56 | League | 2.619 |
| 02/17/07 | Lost | Roosevelt 49 | Garfield 52 | Playoff | 6.543 |
| 02/20/07 | Lost | Roosevelt 36 | Redmond 39 | Playoff | 3.468 |
| 01/04/08 | Won | Roosevelt 72 | Garfield 59 | League | 0.817 |
| 01/25/08 | Lost | Roosevelt 39 | Woodinville 40 | League | 14.797 |
| 02/01/08 | Lost | Roosevelt 40 | Juanita 51 | League | 3.620 |
| 02/21/08 | Lost | Roosevelt 40 | Bothell 42 | Playoff | 5.451 |
| 12/12/08 | Lost | Roosevelt 37 | Woodinville 38 | League | 4.822 |
| 01/06/09 | Won | Roosevelt 48 | Issaquah 47 | League | 2.548 |
| 01/16/09 | Lost | Roosevelt 51 | Ballard 58 | League | 4.740 |
| 01/27/09 | Won | Roosevelt 54 | Redmond 51 | League | 3.222 |
| 02/06/09 | Won | Roosevelt 46 | Inglemoor 43 | League | 6.304 |
| 02/10/09 | Lost | Roosevelt 39 | Lake Washington 53 | League | 2.835 |
| 02/13/09 | Lost | Roosevelt 49 | Ballard 57 | League | 4.740 |
| 02/24/09 | Won | Roosevelt 56 | Issaquah 53 | Playoff | 2.548 |
| 12/11/09 | Won | Roosevelt 36 | Woodinville 32 | League | 3.648 |
| 12/22/09 | Won | Roosevelt 47 | Bothell 40 | League | 2.407 |
| 01/05/10 | Lost | Roosevelt 39 | Issaquah 57 | League | 5.069 |
| 01/26/10 | Lost | Roosevelt 52 | Redmond 63 | League | 5.001 |
| 12/22/10 | Lost | Roosevelt 50 | Shorecrest 56 | Non-league | 7.607 |
| 01/07/11 | Won | Roosevelt 40 | Woodinville 39 | League | 6.896 |
| 01/22/11 | Won | Roosevelt 58 | Eastlake 36 | League | 2.674 |
| 02/01/11 | Won | Roosevelt 50 | Woodinville 46 | League | 6.896 |
| 01/24/12 | Lost | Roosevelt 62 | Bothell 63 | League | 5.235 |
| 02/07/12 | Lost | Roosevelt 38 | Issaquah 49 | Playoff | 0.255 |
| 02/10/12 | Won | Roosevelt 39 | Skyline 38 | Playoff | 3.702 |
| 02/14/12 | Won | Roosevelt 45 | Redmond 42 | Playoff | 0.550 |
| 02/16/12 | Lost | Roosevelt 55 | Bothell 65 | Playoff | 5.235 |
| 12/07/12 | Won | Roosevelt 40 | Skyline 39 | League | 1.822 |
| 01/26/13 | Won | Roosevelt 52 | Skyline 41 | League | 1.822 |
| 12/06/13 | Lost | Roosevelt 34 | Skyline 40 | League | 5.292 |
| 01/17/14 | Lost | Roosevelt 53 | Ballard 60 | League | 0.522 |
| 02/07/14 | Lost | Roosevelt 39 | Ballard 52 | League | 0.522 |
| 02/20/14 | Lost | Roosevelt 45 | Bothell 50 | Playoff | 1.607 |
| 01/13/15 | Lost | Roosevelt 61 | Bishop Blanchet 66 | League | 3.057 |
| 01/30/15 | Lost | Roosevelt 51 | Chief Sealth 54 | League | 9.807 |
| 02/03/15 | Won | Roosevelt 70 | Lakeside (Seattle) 61 | League | 9.811 |
| 02/12/15 | Lost | Roosevelt 68 | Franklin 73 | Playoff | 0.659 |
| 12/09/15 | Won | Roosevelt 57 | Mountlake Terrace 55 | Non-league | 6.239 |
| 01/08/16 | Lost | Roosevelt 43 | Ballard 54 | League | 0.246 |
| 01/22/16 | Won | Roosevelt 60 | Franklin 54 | League | 15.573 |
| 01/29/16 | Won | Roosevelt 69 | Chief Sealth 57 | League | 0.012 |
| 02/05/16 | Lost | Roosevelt 58 | Ingraham 60 | League | 5.106 |
| 12/02/16 | Lost | Roosevelt 58 | Ingraham 68 | League | 3.378 |
| 12/16/16 | Won | Roosevelt 80 | Franklin 68 | League | 14.499 |
| 01/17/17 | Won | Roosevelt 53 | Ballard 50 | League | 2.655 |
| 11/28/17 | Lost | Roosevelt 59 | Northwest 60 | Non-league | 11.466 |
| 12/28/17 | Won | Roosevelt 49 | Liberty (Issaquah) 45 | Non-league | 5.533 |
| 01/05/18 | Won | Roosevelt 57 | Lakeside (Seattle) 54 | League | 5.330 |
| 11/27/18 | Lost | Roosevelt 52 | Lincoln 55 | Non-league | 4.221 |
| 02/14/19 | Lost | Roosevelt 42 | West Seattle 48 | Playoff | 0.163 |
| 12/13/19 | Lost | Roosevelt 46 | Bainbridge 52 | League | 4.434 |
| 01/03/20 | Lost | Roosevelt 67 | Nathan Hale 73 | League | 0.581 |
| 01/07/20 | Won | Roosevelt 58 | Ingraham 56 | League | 6.101 |
| 01/24/20 | Won | Roosevelt 51 | West Seattle 49 | League | 5.505 |
| 02/07/20 | Lost | Roosevelt 32 | Ballard 35 | League | 1.447 |
| 02/12/20 | Lost | Roosevelt 55 | Nathan Hale 60 | Playoff | 0.581 |
| 02/13/20 | Lost | Roosevelt 48 | Bishop Blanchet 53 | Playoff | 1.368 |