69 Wins, 29 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/02/86 | Won | Olympic 38 | South Kitsap 35 | Non-league | 1.236 |
| 12/23/86 | Won | Olympic 58 | Mount Rainier 53 | Non-league | 3.235 |
| 12/30/86 | Lost | Olympic 45 | Wilson 49 | Non-league | 0.654 |
| 01/15/87 | Won | Olympic 31 | Port Angeles 29 | League | 7.740 |
| 01/27/87 | Won | Olympic 51 | Central Kitsap 47 | League | 0.731 |
| 02/10/87 | Won | Olympic 55 | Bremerton 52 | League | 5.991 |
| 12/30/87 | Won | Olympic W | Bellarmine Prep L | Non-league | 9.853 |
| 01/12/88 | Won | Olympic 60 | Sequim 44 | League | 1.409 |
| 12/27/88 | Won | Olympic 48 | Ballard 42 | Non-league | 3.650 |
| 02/10/89 | Won | Olympic 54 | Bremerton 50 | League | 12.646 |
| 01/30/90 | Won | Olympic 53 | Sequim 45 | League | 6.470 |
| 01/24/92 | Won | Olympic 57 | North Kitsap 46 | League | 1.417 |
| 02/11/92 | Won | Olympic 61 | North Kitsap 57 | League | 1.417 |
| 12/18/92 | Won | Olympic 42 | Aberdeen 39 | Non-league | 2.041 |
| 02/09/93 | Lost | Olympic 35 | North Kitsap 44 | League | 7.895 |
| 02/13/93 | Won | Olympic 47 | Sequim 43 | League | 6.520 |
| 02/19/93 | Won | Olympic 46 | Central Kitsap 31 | League | 5.140 |
| 12/08/93 | Lost | Olympic 46 | Bainbridge 53 | Non-league | 2.667 |
| 12/15/93 | Won | Olympic 44 | Aberdeen 40 | Non-league | 1.186 |
| 01/22/94 | Won | Olympic 42 | Port Angeles 33 | League | 2.781 |
| 02/19/94 | Won | Olympic 52 | Port Angeles 42 | Playoff | 2.781 |
| 03/02/94 | Won | Olympic 44 | Auburn 38 | Playoff | 10.231 |
| 03/09/94 | Won | Olympic 51 | Sammamish 35 | Playoff | 6.477 |
| 03/11/94 | Won | Olympic 62 | Shadle Park 60 | Playoff | 1.417 |
| 12/09/94 | Lost | Olympic 42 | Sequim 56 | Non-league | 1.478 |
| 01/21/95 | Lost | Olympic 47 | North Kitsap 52 | League | 11.098 |
| 02/24/95 | Won | Olympic 42 | Wilson 39 | Playoff | 11.713 |
| 12/01/95 | Won | Olympic 59 | Rogers (Puyallup) 52 | Non-league | 0.119 |
| 12/19/95 | Won | Olympic 57 | Port Angeles 55 | League | 6.339 |
| 02/02/96 | Lost | Olympic 41 | Bremerton 47 | League | 3.541 |
| 02/13/96 | Won | Olympic 65 | Bainbridge 61 | League | 1.472 |
| 01/10/97 | Won | Olympic 65 | Bremerton 63 | League | 2.738 |
| 12/09/97 | Won | Olympic 65 | North Thurston 57 | Non-league | 10.074 |
| 12/16/97 | Lost | Olympic 47 | North Kitsap 55 | League | 15.044 |
| 02/13/98 | Lost | Olympic 49 | Port Townsend 57 | League | 2.282 |
| 02/20/98 | Won | Olympic 75 | Central Kitsap 69 | League | 2.496 |
| 01/25/00 | Won | Olympic 61 | North Kitsap 59 | League | 15.994 |
| 02/15/00 | Won | Olympic 62 | Port Townsend 61 | League | 9.400 |
| 02/06/01 | Won | Olympic 52 | Sequim 46 | League | 17.193 |
| 12/05/01 | Won | Olympic 56 | Foss 54 | Non-league | 10.687 |
| 12/03/02 | Won | Olympic 53 | King's West 46 | Non-league | 8.716 |
| 12/11/02 | Lost | Olympic 34 | Stadium 39 | Non-league | 7.353 |
| 12/03/03 | Lost | Olympic 31 | Peninsula 40 | Non-league | 2.241 |
| 02/13/04 | Won | Olympic 64 | North Kitsap 48 | League | 9.921 |
| 01/06/06 | Won | Olympic 50 | Shelton 48 | League | 1.441 |
| 01/11/06 | Won | Olympic 51 | Bremerton 49 | League | 15.454 |
| 01/18/06 | Won | Olympic 40 | South Kitsap 38 | League | 12.101 |
| 01/31/06 | Won | Olympic 51 | Shelton 38 | League | 1.441 |
| 02/08/06 | Won | Olympic 46 | North Kitsap 41 | League | 11.807 |
| 12/05/06 | Won | Olympic 62 | King's West 55 | Non-league | 1.277 |
| 12/22/06 | Lost | Olympic 46 | North Kitsap 51 | Non-league | 4.496 |
| 11/28/07 | Lost | Olympic 43 | Central Kitsap 46 | Non-league | 4.409 |
| 12/07/07 | Lost | Olympic 49 | Sequim 51 | League | 9.432 |
| 12/11/07 | Won | Olympic 65 | Port Angeles 41 | League | 3.360 |
| 12/14/07 | Won | Olympic 54 | Kingston 48 | League | 4.772 |
| 12/28/07 | Won | Olympic 49 | Aberdeen 38 | Non-league | 2.755 |
| 01/10/08 | Lost | Olympic 50 | Peninsula 55 | League | 2.638 |
| 01/22/08 | Won | Olympic 45 | Port Angeles 44 | League | 3.360 |
| 02/23/08 | Won | Olympic 43 | Mount Rainier 42 | Playoff | 2.947 |
| 12/16/08 | Lost | Olympic 66 | Port Townsend 73 | League | 3.246 |
| 01/20/09 | Won | Olympic 49 | North Kitsap 47 | League | 7.187 |
| 01/23/09 | Lost | Olympic 51 | North Mason 59 | League | 3.582 |
| 02/20/09 | Won | Olympic 56 | North Kitsap 39 | Playoff | 7.187 |
| 12/21/09 | Won | Olympic 42 | Central Kitsap 35 | Non-league | 10.981 |
| 12/17/10 | Lost | Olympic 54 | Port Townsend 55 | League | 9.933 |
| 12/18/10 | Won | Olympic 53 | Peninsula 45 | Non-league | 1.504 |
| 02/21/11 | Won | Olympic 42 | Kingston 40 | Playoff | 11.475 |
| 12/28/11 | Won | Olympic 50 | Tumwater 48 | Non-league | 6.428 |
| 01/27/12 | Lost | Olympic 33 | Port Townsend 37 | League | 19.378 |
| 01/31/12 | Won | Olympic 56 | Bremerton 43 | League | 5.507 |
| 11/27/12 | Won | Olympic 40 | Gig Harbor 38 | Non-league | 5.080 |
| 12/21/12 | Lost | Olympic 48 | Bremerton 61 | League | 0.345 |
| 02/05/13 | Won | Olympic 62 | North Kitsap 48 | League | 0.104 |
| 12/11/13 | Lost | Olympic 45 | Sequim 52 | League | 5.106 |
| 12/18/13 | Won | Olympic 42 | Kingston 34 | League | 3.930 |
| 02/11/14 | Lost | Olympic 56 | North Kitsap 66 | League | 3.080 |
| 02/22/14 | Won | Olympic 43 | Kingston 40 | Playoff | 3.930 |
| 12/22/14 | Won | Olympic 52 | Gig Harbor 43 | Non-league | 7.784 |
| 01/30/15 | Won | Olympic 50 | Kingston 49 | League | 3.086 |
| 02/13/15 | Won | Olympic 50 | Franklin Pierce 43 | Playoff | 0.558 |
| 12/16/15 | Won | Olympic 59 | North Kitsap 50 | League | 5.941 |
| 12/23/15 | Won | Olympic 53 | Central Kitsap 47 | Non-league | 5.316 |
| 01/08/16 | Won | Olympic 40 | Kingston 35 | League | 3.432 |
| 01/15/16 | Won | Olympic 46 | Port Angeles 27 | League | 1.393 |
| 01/29/16 | Won | Olympic 40 | Kingston 35 | League | 3.432 |
| 12/20/16 | Lost | Olympic 50 | Central Kitsap 60 | Non-league | 3.631 |
| 01/13/17 | Lost | Olympic 43 | Kingston 46 | League | 5.886 |
| 01/31/17 | Lost | Olympic 33 | Port Angeles 45 | League | 1.618 |
| 02/02/17 | Won | Olympic 63 | North Kitsap 34 | League | 3.163 |
| 02/11/17 | Lost | Olympic 39 | Franklin Pierce 43 | Playoff | 0.910 |
| 11/30/17 | Won | Olympic 46 | Cascade Christian (Puyallup) 41 | Non-league | 0.680 |
| 12/22/17 | Lost | Olympic 37 | Central Kitsap 50 | Non-league | 2.410 |
| 01/23/18 | Won | Olympic 59 | Kingston 43 | League | 3.612 |
| 02/07/18 | Lost | Olympic 58 | Eatonville 63 | Playoff | 11.523 |
| 01/08/19 | Lost | Olympic 48 | Kingston 59 | League | 2.394 |
| 01/29/19 | Won | Olympic 49 | Sequim 45 | League | 17.089 |
| 01/31/19 | Lost | Olympic 51 | Kingston 54 | League | 2.394 |
| 02/06/20 | Won | Olympic 50 | Kingston 46 | League | 5.231 |
36 Wins, 35 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 01/08/03 | Won | Olympic 57 | Shelton 56 | League | 5.111 |
| 01/10/03 | Won | Olympic 59 | Central Kitsap 45 | League | 3.665 |
| 01/24/03 | Won | Olympic 55 | Port Angeles 42 | League | 1.220 |
| 02/14/03 | Lost | Olympic 60 | North Kitsap 64 | League | 5.693 |
| 12/02/03 | Won | Olympic 61 | Stadium 55 | Non-league | 2.175 |
| 12/17/03 | Lost | Olympic 49 | Port Angeles 50 | League | 0.426 |
| 01/09/04 | Lost | Olympic 51 | Shelton 54 | League | 2.636 |
| 01/14/04 | Won | Olympic 58 | Central Kitsap 55 | League | 14.301 |
| 01/28/04 | Lost | Olympic 57 | Gig Harbor 60 | League | 1.558 |
| 01/30/04 | Won | Olympic 71 | Bremerton 66 | League | 2.673 |
| 02/13/04 | Lost | Olympic 74 | North Kitsap 80 | League | 5.899 |
| 02/17/04 | Lost | Olympic 74 | Shelton 78 | Playoff | 2.636 |
| 12/21/04 | Won | Olympic 84 | Stadium 70 | Non-league | 11.447 |
| 01/07/05 | Won | Olympic 59 | Shelton 48 | League | 8.265 |
| 01/06/06 | Lost | Olympic 42 | Shelton 43 | League | 0.893 |
| 01/13/06 | Won | Olympic 46 | North Kitsap 44 | League | 0.976 |
| 02/08/06 | Won | Olympic 62 | North Kitsap 54 | League | 0.976 |
| 01/20/07 | Lost | Olympic 68 | Bremerton 79 | League | 8.659 |
| 01/22/07 | Won | Olympic 77 | Port Angeles 63 | League | 5.425 |
| 01/23/07 | Lost | Olympic 73 | Klahowya 76 | League | 15.008 |
| 12/31/08 | Lost | Olympic 45 | Sumner 49 | Non-league | 1.254 |
| 01/30/09 | Won | Olympic 68 | Klahowya 60 | League | 0.285 |
| 12/04/09 | Lost | Olympic 39 | North Kitsap 40 | League | 2.699 |
| 12/15/09 | Lost | Olympic 47 | Port Townsend 48 | League | 5.299 |
| 12/22/09 | Won | Olympic 47 | Shelton 38 | Non-league | 0.740 |
| 01/08/10 | Won | Olympic 38 | Kingston 37 | League | 4.387 |
| 01/29/10 | Lost | Olympic 40 | Klahowya 41 | League | 14.533 |
| 02/09/10 | Won | Olympic 59 | Kingston 52 | League | 4.387 |
| 02/12/10 | Won | Olympic 47 | Port Angeles 41 | League | 3.456 |
| 12/03/10 | Won | Olympic 49 | Sequim 42 | League | 3.340 |
| 01/18/11 | Won | Olympic 57 | Port Angeles 53 | League | 10.157 |
| 01/28/11 | Lost | Olympic 58 | Port Townsend 63 | League | 5.256 |
| 02/01/11 | Won | Olympic 62 | Bremerton 59 | League | 6.069 |
| 12/20/11 | Lost | Olympic 48 | Bremerton 57 | League | 6.278 |
| 01/10/12 | Won | Olympic 73 | Kingston 62 | League | 10.783 |
| 01/31/12 | Lost | Olympic 68 | Bremerton 75 | League | 6.278 |
| 01/05/13 | Lost | Olympic 50 | Auburn Mountainview 59 | Non-league | 7.868 |
| 01/11/13 | Lost | Olympic 54 | Sequim 67 | League | 5.894 |
| 02/15/13 | Lost | Olympic 66 | White River 69 | Playoff | 3.778 |
| 12/06/13 | Lost | Olympic 72 | Port Angeles 74 | League | 9.204 |
| 12/11/13 | Lost | Olympic 50 | Sequim 57 | League | 3.046 |
| 12/16/13 | Won | Olympic 49 | Auburn Mountainview 46 | Non-league | 2.215 |
| 01/17/14 | Lost | Olympic 55 | Sequim 57 | League | 3.046 |
| 02/07/14 | Won | Olympic 63 | Bremerton 55 | League | 1.626 |
| 02/17/14 | Won | Olympic 54 | Steilacoom 42 | Playoff | 2.385 |
| 12/01/14 | Lost | Olympic 51 | Central Kitsap 58 | Non-league | 6.902 |
| 12/17/14 | Won | Olympic 78 | North Kitsap 75 | League | 0.250 |
| 01/23/15 | Lost | Olympic 39 | Sequim 51 | League | 4.096 |
| 02/17/15 | Won | Olympic 61 | Clover Park 59 | Playoff | 0.441 |
| 02/28/15 | Won | Olympic 45 | East Valley (Yakima) 43 | Playoff | 1.411 |
| 12/07/15 | Lost | Olympic 56 | Capital 66 | Non-league | 0.696 |
| 12/14/15 | Lost | Olympic 51 | Port Angeles 54 | League | 6.501 |
| 12/23/15 | Lost | Olympic 64 | Central Kitsap 72 | Non-league | 3.871 |
| 01/19/16 | Won | Olympic 67 | North Kitsap 63 | League | 8.394 |
| 12/07/16 | Lost | Olympic 62 | Kingston 67 | League | 0.010 |
| 12/13/16 | Lost | Olympic 69 | Cascade Christian (Puyallup) 73 | Non-league | 10.671 |
| 01/31/17 | Lost | Olympic 60 | Port Angeles 62 | League | 6.908 |
| 02/02/17 | Won | Olympic 65 | North Kitsap 62 | League | 2.004 |
| 02/25/17 | Won | Olympic 56 | Lynden 47 | Playoff | 7.115 |
| 12/02/17 | Won | Olympic 72 | Kennedy Catholic 50 | Non-league | 3.559 |
| 12/29/17 | Won | Olympic 59 | Clover Park 55 | Non-league | 0.340 |
| 01/05/18 | Lost | Olympic 39 | Port Angeles 50 | League | 0.210 |
| 01/12/18 | Won | Olympic 55 | North Kitsap 50 | League | 9.624 |
| 11/27/18 | Lost | Olympic 56 | Peninsula 64 | Non-league | 0.232 |
| 12/07/18 | Lost | Olympic 49 | Bremerton 52 | League | 15.165 |
| 01/29/19 | Lost | Olympic 47 | Sequim 51 | League | 6.111 |
| 02/06/19 | Won | Olympic 81 | Foster 54 | Playoff | 8.067 |
| 02/16/19 | Won | Olympic 51 | Port Angeles 48 | Playoff | 13.539 |
| 12/04/19 | Won | Olympic 65 | Peninsula 53 | Non-league | 3.340 |
| 01/10/20 | Lost | Olympic 49 | Sequim 51 | League | 5.405 |
| 01/22/20 | Won | Olympic 64 | Bremerton 56 | League | 4.613 |