51 Wins, 53 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 01/09/87 | Lost | Orcas Island 62 | Lopez 63 | League | 1.765 |
| 02/10/87 | Lost | Orcas Island 37 | Lopez 46 | League | 1.765 |
| 01/08/88 | Won | Orcas Island 52 | Lopez 40 | Non-league | 1.611 |
| 01/23/88 | Won | Orcas Island 49 | Friday Harbor 45 | League | 0.951 |
| 02/09/88 | Won | Orcas Island 49 | Darrington 32 | League | 1.677 |
| 01/24/89 | Lost | Orcas Island 35 | Friday Harbor 53 | League | 2.793 |
| 02/03/89 | Lost | Orcas Island 44 | La Conner 60 | League | 13.600 |
| 02/04/89 | Lost | Orcas Island 37 | Watson Groen Christian 39 | League | 1.692 |
| 02/18/89 | Lost | Orcas Island 41 | Watson Groen Christian 50 | Playoff | 1.692 |
| 12/09/89 | Lost | Orcas Island 45 | Darrington 47 | League | 1.510 |
| 12/16/89 | Lost | Orcas Island 44 | Watson Groen Christian 46 | League | 13.418 |
| 03/01/90 | Won | Orcas Island 68 | Neah Bay 58 | Playoff | 0.857 |
| 12/15/90 | Lost | Orcas Island 41 | Bellevue Christian 48 | Non-league | 3.099 |
| 01/11/91 | Lost | Orcas Island 58 | La Conner 71 | League | 1.427 |
| 01/19/91 | Won | Orcas Island 70 | Darrington 55 | League | 19.579 |
| 02/02/91 | Lost | Orcas Island 43 | Watson Groen Christian 53 | League | 11.901 |
| 02/21/92 | Won | Orcas Island 65 | Seattle Lutheran 63 | Playoff | 16.419 |
| 02/28/92 | Won | Orcas Island 53 | Darrington 51 | Playoff | 12.010 |
| 01/05/93 | Lost | Orcas Island 35 | La Conner 47 | League | 1.591 |
| 01/23/93 | Lost | Orcas Island 38 | Darrington 50 | League | 0.522 |
| 02/23/93 | Won | Orcas Island 53 | Seattle Lutheran 52 | Playoff | 6.572 |
| 02/04/94 | Lost | Orcas Island 31 | Snohomish County Christian 35 | League | 11.312 |
| 02/05/94 | Lost | Orcas Island 40 | Darrington 50 | League | 1.584 |
| 12/13/94 | Won | Orcas Island 57 | Lopez 45 | Non-league | 6.076 |
| 02/11/95 | Lost | Orcas Island 43 | Mount Vernon Christian 48 | Playoff | 1.480 |
| 01/11/96 | Lost | Orcas Island 53 | Snohomish County Christian 57 | League | 1.994 |
| 01/23/96 | Lost | Orcas Island 42 | La Conner 50 | League | 3.205 |
| 01/26/96 | Won | Orcas Island 42 | Watson Groen Christian 40 | League | 15.447 |
| 01/27/96 | Won | Orcas Island 51 | Coupeville 36 | Non-league | 1.962 |
| 02/05/96 | Lost | Orcas Island 36 | Snohomish County Christian 39 | League | 1.994 |
| 12/10/96 | Won | Orcas Island 44 | Lopez 42 | Non-league | 7.328 |
| 01/04/97 | Lost | Orcas Island 36 | Tacoma Baptist 52 | Non-league | 2.237 |
| 01/20/98 | Won | Orcas Island 44 | Darrington 31 | League | 2.387 |
| 01/27/98 | Won | Orcas Island 47 | Coupeville 43 | League | 6.969 |
| 02/10/98 | Won | Orcas Island 58 | Shoreline Christian 41 | League | 3.497 |
| 02/12/98 | Won | Orcas Island 41 | Shoreline Christian 40 | Playoff | 3.497 |
| 02/27/98 | Won | Orcas Island 51 | King's West 36 | Playoff | 8.866 |
| 01/15/99 | Lost | Orcas Island 35 | Shoreline Christian 45 | League | 0.666 |
| 01/26/99 | Lost | Orcas Island 47 | Coupeville 55 | League | 5.899 |
| 02/02/99 | Lost | Orcas Island 38 | Snohomish County Christian 39 | League | 3.254 |
| 02/09/99 | Lost | Orcas Island 40 | Shoreline Christian 52 | League | 0.666 |
| 02/20/99 | Lost | Orcas Island 50 | Seattle Lutheran 66 | Playoff | 0.563 |
| 02/08/00 | Lost | Orcas Island 42 | La Conner 50 | League | 0.212 |
| 01/06/01 | Lost | Orcas Island 32 | Friday Harbor 48 | League | 7.211 |
| 02/06/01 | Won | Orcas Island 50 | La Conner 39 | League | 11.794 |
| 02/02/02 | Lost | Orcas Island 32 | Friday Harbor 38 | League | 0.347 |
| 12/06/02 | Lost | Orcas Island 24 | Seattle Academy 34 | Non-league | 13.261 |
| 12/30/02 | Won | Orcas Island 61 | Nathan Hale 48 | Non-league | 5.410 |
| 01/07/03 | Lost | Orcas Island 45 | La Conner 50 | League | 6.366 |
| 12/12/03 | Lost | Orcas Island 48 | Mount Vernon Christian 55 | Non-league | 0.390 |
| 02/09/04 | Won | Orcas Island 57 | Archbishop Murphy 54 | League | 18.805 |
| 12/18/04 | Won | Orcas Island 43 | Friday Harbor 36 | League | 5.743 |
| 12/29/04 | Won | Orcas Island 73 | Cle Elum-Roslyn 68 | Non-league | 9.007 |
| 01/11/05 | Won | Orcas Island 41 | Mount Vernon Christian 38 | League | 1.283 |
| 02/01/05 | Won | Orcas Island 45 | Darrington 41 | League | 6.977 |
| 12/06/05 | Lost | Orcas Island 31 | Darrington 34 | League | 5.104 |
| 12/11/06 | Won | Orcas Island 45 | Meridian 42 | Non-league | 4.326 |
| 12/29/06 | Lost | Orcas Island 45 | Life Christian 46 | Non-league | 0.359 |
| 12/30/06 | Won | Orcas Island 37 | Forest Ridge 26 | Non-league | 1.181 |
| 01/02/07 | Won | Orcas Island 43 | La Conner 39 | League | 1.800 |
| 01/23/07 | Won | Orcas Island 46 | Concrete 43 | League | 10.077 |
| 01/26/07 | Won | Orcas Island 53 | La Conner 49 | League | 1.800 |
| 02/06/07 | Lost | Orcas Island 27 | Mount Vernon Christian 34 | League | 2.965 |
| 02/17/07 | Lost | Orcas Island 39 | Life Christian 46 | Playoff | 0.359 |
| 12/18/07 | Lost | Orcas Island 47 | La Conner 52 | League | 2.321 |
| 02/22/08 | Lost | Orcas Island 26 | La Conner 27 | Playoff | 2.321 |
| 02/23/08 | Lost | Orcas Island 43 | Seattle Lutheran 55 | Playoff | 7.852 |
| 01/06/09 | Lost | Orcas Island 40 | Shoreline Christian 49 | League | 5.499 |
| 01/23/09 | Lost | Orcas Island 47 | Concrete 49 | League | 11.662 |
| 01/24/09 | Lost | Orcas Island 26 | Mount Vernon Christian 35 | League | 3.649 |
| 02/10/09 | Won | Orcas Island 36 | La Conner 27 | League | 1.219 |
| 02/28/09 | Won | Orcas Island 44 | La Conner 39 | Playoff | 1.219 |
| 03/05/09 | Won | Orcas Island 37 | Garfield-Palouse 30 | Playoff | 9.857 |
| 03/07/09 | Won | Orcas Island 40 | Pomeroy 39 | Playoff | 7.947 |
| 12/08/09 | Lost | Orcas Island 12 | Lopez 36 | Non-league | 30.361 |
| 12/19/09 | Won | Orcas Island 34 | Mossyrock 31 | Non-league | 8.240 |
| 01/12/10 | Won | Orcas Island 42 | Darrington 37 | League | 8.738 |
| 02/06/10 | Won | Orcas Island 55 | Darrington 45 | League | 8.738 |
| 02/26/10 | Won | Orcas Island 36 | La Conner 31 | Playoff | 4.423 |
| 12/21/10 | Won | Orcas Island 41 | Evergreen Lutheran 34 | Non-league | 4.832 |
| 01/08/11 | Won | Orcas Island 48 | Shoreline Christian 39 | League | 6.613 |
| 01/29/11 | Won | Orcas Island 40 | Concrete 33 | League | 2.111 |
| 02/04/11 | Won | Orcas Island 48 | La Conner 43 | League | 9.343 |
| 01/25/12 | Won | Orcas Island 48 | Concrete 42 | League | 1.304 |
| 02/02/12 | Lost | Orcas Island 37 | Mount Vernon Christian 44 | League | 2.583 |
| 12/22/12 | Lost | Orcas Island 31 | Coupeville 39 | Non-league | 2.788 |
| 01/18/13 | Lost | Orcas Island 47 | Mount Vernon Christian 56 | League | 0.796 |
| 02/01/13 | Won | Orcas Island 54 | Darrington 39 | League | 4.806 |
| 02/07/13 | Lost | Orcas Island 36 | Crosspoint 50 | Playoff | 2.185 |
| 01/14/14 | Lost | Orcas Island 41 | Darrington 45 | Non-league | 1.991 |
| 02/22/14 | Lost | Orcas Island 53 | Crosspoint 60 | Playoff | 1.028 |
| 01/03/15 | Lost | Orcas Island 33 | Manson 39 | Non-league | 6.748 |
| 01/27/15 | Won | Orcas Island 48 | Friday Harbor 41 | League | 5.216 |
| 12/11/15 | Won | Orcas Island 48 | Mount Vernon Christian 44 | League | 10.059 |
| 01/03/17 | Won | Orcas Island 45 | Friday Harbor 38 | League | 2.348 |
| 01/26/17 | Won | Orcas Island 45 | Friday Harbor 41 | League | 2.348 |
| 02/10/17 | Lost | Orcas Island 41 | Auburn Adventist 43 | Playoff | 10.844 |
| 12/20/17 | Lost | Orcas Island 34 | Auburn Adventist 37 | Non-league | 11.540 |
| 12/28/17 | Won | Orcas Island 74 | Clallam Bay 59 | Non-league | 0.306 |
| 12/29/17 | Won | Orcas Island 47 | Coupeville 44 | Non-league | 1.203 |
| 01/19/18 | Won | Orcas Island 40 | Mount Vernon Christian 37 | League | 10.847 |
| 12/08/18 | Won | Orcas Island 31 | Coupeville 27 | Non-league | 3.422 |
| 01/04/20 | Lost | Orcas Island 44 | South Whidbey 49 | Non-league | 4.685 |
| 02/01/20 | Lost | Orcas Island 43 | Lopez 56 | Non-league | 13.219 |
34 Wins, 19 Losses
| Date | Game Type | Upset Magnitude | |||
|---|---|---|---|---|---|
| 12/06/02 | Lost | Orcas Island 29 | Seattle Academy 38 | Non-league | 6.799 |
| 12/20/02 | Won | Orcas Island 63 | Cedar Park Christian (Bothell) 57 | Non-league | 1.904 |
| 12/27/02 | Won | Orcas Island 68 | Mount Vernon Christian 67 | Non-league | 2.050 |
| 01/10/03 | Lost | Orcas Island 52 | Coupeville 58 | League | 8.087 |
| 01/24/03 | Lost | Orcas Island 41 | Archbishop Murphy 57 | League | 3.454 |
| 02/22/03 | Lost | Orcas Island 39 | Charles Wright 46 | Playoff | 0.340 |
| 02/25/03 | Won | Orcas Island 50 | Cedar Park Christian (Bothell) 44 | Playoff | 1.904 |
| 02/27/03 | Won | Orcas Island 54 | La Conner 48 | Playoff | 7.735 |
| 03/01/03 | Won | Orcas Island 65 | King's 59 | Playoff | 17.109 |
| 03/06/03 | Won | Orcas Island 57 | White Swan 54 | Playoff | 11.799 |
| 12/14/04 | Won | Orcas Island 51 | Concrete 41 | League | 0.103 |
| 12/29/04 | Lost | Orcas Island 36 | Cle Elum-Roslyn 51 | Non-league | 3.501 |
| 01/21/05 | Won | Orcas Island 51 | Concrete 49 | League | 0.103 |
| 12/01/05 | Lost | Orcas Island 48 | Seattle Academy 52 | Non-league | 2.577 |
| 12/03/05 | Won | Orcas Island 58 | Sultan 54 | Non-league | 6.353 |
| 12/06/05 | Won | Orcas Island 43 | Darrington 36 | League | 2.049 |
| 12/10/05 | Won | Orcas Island 61 | Bush 39 | Non-league | 0.243 |
| 02/03/06 | Won | Orcas Island 60 | Shoreline Christian 59 | League | 1.491 |
| 02/06/06 | Won | Orcas Island 75 | Shoreline Christian 55 | Playoff | 1.491 |
| 12/07/06 | Lost | Orcas Island 46 | Lopez 48 | Non-league | 13.528 |
| 01/20/07 | Won | Orcas Island 50 | Friday Harbor 45 | League | 13.793 |
| 02/06/07 | Won | Orcas Island 60 | Mount Vernon Christian 58 | League | 8.639 |
| 02/13/07 | Lost | Orcas Island 58 | Quilcene 61 | Playoff | 6.790 |
| 12/14/07 | Won | Orcas Island 60 | Concrete 50 | League | 6.768 |
| 01/12/08 | Lost | Orcas Island 44 | Mount Vernon Christian 47 | League | 4.406 |
| 01/30/09 | Won | Orcas Island 40 | Shoreline Christian 29 | League | 3.732 |
| 01/31/09 | Won | Orcas Island 57 | Mount Vernon Christian 48 | League | 7.368 |
| 12/11/09 | Won | Orcas Island 47 | Granite Falls 42 | Non-league | 1.810 |
| 12/15/09 | Won | Orcas Island 60 | Concrete 57 | League | 0.464 |
| 12/17/09 | Won | Orcas Island 65 | Mount Vernon Christian 45 | League | 3.161 |
| 01/09/10 | Won | Orcas Island 63 | Lopez 47 | Non-league | 2.944 |
| 01/21/11 | Won | Orcas Island 57 | Darrington 52 | League | 6.094 |
| 01/06/12 | Won | Orcas Island 54 | Mount Vernon Christian 49 | League | 2.839 |
| 12/19/12 | Won | Orcas Island 62 | Concrete 49 | Non-league | 9.576 |
| 12/22/12 | Won | Orcas Island 66 | Coupeville 61 | Non-league | 0.830 |
| 01/18/13 | Lost | Orcas Island 58 | Mount Vernon Christian 69 | League | 1.617 |
| 01/21/14 | Won | Orcas Island 85 | Shoreline Christian 63 | League | 1.320 |
| 12/09/14 | Won | Orcas Island 59 | Cedar Park Christian (Mountlake Terrace) 47 | League | 2.983 |
| 12/09/15 | Lost | Orcas Island 71 | Coupeville 74 | Non-league | 7.086 |
| 12/17/15 | Lost | Orcas Island 54 | Auburn Adventist 63 | Non-league | 6.858 |
| 01/05/16 | Won | Orcas Island 58 | Friday Harbor 56 | League | 15.196 |
| 02/02/16 | Lost | Orcas Island 66 | Shoreline Christian 81 | League | 16.923 |
| 12/16/16 | Lost | Orcas Island 51 | Bear Creek 69 | Non-league | 5.301 |
| 01/20/17 | Lost | Orcas Island 62 | La Conner 66 | League | 11.631 |
| 02/16/17 | Won | Orcas Island 65 | Seattle Lutheran 50 | Playoff | 1.348 |
| 02/25/17 | Lost | Orcas Island 60 | Chief Leschi 65 | Playoff | 2.236 |
| 12/19/17 | Lost | Orcas Island 54 | Mount Vernon Christian 65 | League | 9.980 |
| 02/13/18 | Lost | Orcas Island 76 | Crosspoint 79 | Playoff | 5.040 |
| 12/08/18 | Won | Orcas Island 48 | Coupeville 40 | Non-league | 5.442 |
| 01/15/19 | Won | Orcas Island 57 | Concrete 56 | League | 0.355 |
| 02/05/19 | Won | Orcas Island 58 | Concrete 47 | League | 0.355 |
| 01/10/20 | Won | Orcas Island 55 | Friday Harbor 47 | League | 0.562 |
| 01/17/20 | Lost | Orcas Island 51 | Mount Vernon Christian 53 | League | 0.107 |