| Monday, November 25, 2019 |
| Wrestling 1st Practice | 4:00 pm | SHS | |
| Tuesday, December 10, 2019 |
| Wrestling vs Blue/Gold Dual | 5:00 pm | SJHS | |
| Thursday, December 12, 2019 |
| Wrestling vs Worland Varsity only | 5:00 pm | Sheridan | |
| Friday, December 13, 2019 to Friday, December 13, 2019 |
| Wrestling JV @ Powell Tourney | All Day | Powell | |
| Wrestling V @ Rapid City Invite | All Day | Rapid City | |
| Friday, December 20, 2019 to Saturday, December 21, 2019 |
| Wrestling @ Wasatch Intermountain Duals | All Day | | Varsity Only |
| Friday, December 20, 2019 to Friday, December 20, 2019 |
| Wrestling @ Worland Duals | All Day | Worland | |
| Saturday, December 21, 2019 to Saturday, December 21, 2019 |
| Wrestling @ Worland Duals | All Day | Sheridan | |
| Friday, January 10, 2020 to Saturday, January 11, 2020 |
| Wrestling @ Shane Shatto Invite | All Day | Douglas | |
| Thursday, January 16, 2020 |
| Wrestling @ Colstrip Dual | 3:00 pm | Colstrip | Time TBA |
| Friday, January 17, 2020 to Saturday, January 18, 2020 |
| Wrestling @ Cowboy Invite | All Day | Miles City | |
| Friday, January 17, 2020 to Friday, January 17, 2020 |
| Wrestling JV @ Newcastle Invite | All Day | Newcastle | |
| Saturday, January 18, 2020 |
| Wrestling vs Border Wars | 10:00 am | Sheridan | Billings (West, Skyview, Senior), Colstrip, South, Thunder |
| Friday, January 24, 2020 to Saturday, January 25, 2020 |
| Wrestling @ Moorcroft Invite | All Day | Moorcroft | |
| Thursday, January 30, 2020 to Thursday, January 30, 2020 |
| Wrestling @ Natrona | All Day | Casper | stop on way to Ron Thon |
| Friday, January 31, 2020 to Saturday, February 1, 2020 |
| Wrestling @ Ron Thon Tourney | All Day | Riverton | |
| Friday, February 7, 2020 |
| Wrestling vs East/Central | 4:00 - 5:30 pm | Sheridan | |
| Saturday, February 8, 2020 |
| Wrestling vs South | 10:00 - 12:00 pm | Sheridan | |
| Thursday, February 13, 2020 |
| Wrestling vs Campbell County Dual | 5:00 - 6:00 pm | Sheridan | |
| Saturday, February 15, 2020 |
| Wrestling @ Thunder Basin Dual | 4:00 pm | Thunder Basin | Try to find another time. |
| Friday, February 21, 2020 to Saturday, February 22, 2020 |
| Wrestling @ Regionals | All Day | Central | |
| Friday, February 28, 2020 to Saturday, February 29, 2020 |
| Wrestling @ State Tournament | All Day | Casper | |
