| 2022 (1) Hilldale over McLain 32-0 |
| 2022 (Q) Elk City over Hilldale 24-20 |
| 2021 (1) Wagoner over Hilldale 37-35 |
| 2020 (1) Hilldale over Miami 42-0 |
| 2020 (2) Hilldale over Grove 43-42 |
| 2020 (Q) Cushing over Hilldale 34-28 |
| 2018 (1) Hilldale over Bristow 35-21 |
| 2018 (Q) Tuttle over Hilldale 42-14 |
| 2017 (1) Hilldale over Catoosa 37-14 |
| 2017 (Q) Bethany over Hilldale 21-17 |
| 2016 (1) Hilldale over Catoosa 51-7 |
| 2016 (Q) Clinton over Hilldale 36-29 |
| 2015 (1) Hilldale over Sperry 62-13 |
| 2015 (2) Hilldale over Sequoyah Tahlequah 57-21 |
| 2015 (Q) Heritage Hall over Hilldale 41-6 |
| 2014 (1) Lincoln Christian over Hilldale 57-15 |
| 2013 (1) Hilldale over Spiro 32-7 |
| 2013 (2) Hilldale over Metro Christian 14-12 |
| 2013 (Q) Seminole over Hilldale 43-28 |
| 2012 (1) Hilldale over Checotah 35-0 |
| 2012 (2) Hilldale over Verdigris 36-23 |
| 2012 (Q) Blanchard over Hilldale 42-0 |
| 2011 (1) Hilldale over McLain 22-12 |
| 2011 (Q) Clinton over Hilldale 49-14 |
| 2010 (1) Oologah over Hilldale 51-26 |
| 2007 (1) Grove over Hilldale 23-0 |
| 2006 (1) Wagoner over Hilldale 21-7 |
| 2005 (1) Hilldale over Oologah 27-17 |
| 2005 (Q) Star Spencer over Hilldale 28-20 |
| 2004 (1) Hilldale over Miami 21-20 |
| 2004 (Q) Clinton over Hilldale 37-0 |
| 2003 (1) Berryhill over Hilldale 38-7 |
| 1993 (1) Sulphur over Hilldale 42-6 |
| 1991 (1) Henryetta over Hilldale 9-7 |
| 1987 (1) Hilldale over Cushing 21-8 |
| 1987 (2) Broken Bow over Hilldale 14-12 |
| 1985 (1) Hilldale over Inola 29-8 |
| 1985 (2) Wilburton over Hilldale 9-7 |
| 1981 (1) Afton over Hilldale 15-6 |