| Monday, November 25, 2019 |
| Boys Basketball vs First Practice | 4:00 pm | SHS | |
| Thursday, December 12, 2019 to Saturday, December 14, 2019 |
| JV Boys Basketball @ East/West Tourney | All Day | Casper | |
| Varsity Boys Basketball @ East/West Tourney | All Day | Casper | |
| Soph Boys Basketball @ East/West Tourney | All Day | Casper | |
| Friday, December 20, 2019 |
| Soph Boys Basketball @ Billings Skyview | 4:00 pm | Billings | |
| JV Boys Basketball @ Billings Skyview | 5:30 pm | Billings | |
| Varsity Boys Basketball @ Billings Skyview | 7:00 pm | Billings | |
| Saturday, December 21, 2019 |
| JV Boys Basketball vs Buffalo | 11:00 - 12:00 pm | Sheridan | |
| Soph Boys Basketball vs Buffalo | 12:30 - 1:30 pm | Sheridan | |
| Varsity Boys Basketball vs Buffalo | 2:00 - 3:00 pm | Sheridan | |
| Thursday, January 9, 2020 to Saturday, January 11, 2020 |
| Soph Boys Basketball @ Cheyenne Tourney | All Day | Cheyenne | |
| JV Boys Basketball @ Cheyenne Tourney | All Day | Cheyenne | |
| Varsity Boys Basketball @ Cheyenne Tourney | All Day | Cheyenne | |
| Thursday, January 16, 2020 |
| JV Boys Basketball @ Kelly Walsh | 4:00 pm | Kelly Walsh | |
| Soph Boys Basketball @ Kelly Walsh | 5:30 pm | Kelly Walsh | |
| Varsity Boys Basketball @ Kelly Walsh | 7:00 pm | Kelly Walsh | |
| Friday, January 17, 2020 |
| Soph Boys Basketball vs Billings Skyview | 4:00 pm | Sheridan | |
| JV Boys Basketball vs Billings Skyview | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs Billings Skyview | 7:00 pm | Sheridan | |
| Friday, January 24, 2020 |
| JV Boys Basketball vs Thunder Basin | 4:00 pm | Sheridan | |
| Soph Boys Basketball vs Thunder Basin | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs Thunder Basin | 7:00 pm | Sheridan | |
| Saturday, January 25, 2020 |
| Soph Boys Basketball @ Campbell County | 3:00 - 4:00 pm | Gillette | |
| JV Boys Basketball @ Campbell County | 4:30 - 5:30 pm | Gillette | |
| Varsity Boys Basketball @ Campbell County | 7:30 - 8:30 pm | Gillette | |
| Friday, January 31, 2020 |
| JV Boys Basketball vs Natrona | 4:00 pm | Sheridan | |
| Soph Boys Basketball vs Natrona | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs Natrona | 7:00 pm | Sheridan | |
| Friday, February 7, 2020 |
| JV Boys Basketball @ Cheyenne Central | 4:00 pm | Cheyenne | |
| Soph Boys Basketball @ Cheyenne Central | 5:30 pm | Cheyenne | |
| Varsity Boys Basketball @ Cheyenne Central | 7:00 pm | Cheyenne | |
| Saturday, February 8, 2020 |
| JV Boys Basketball @ Cheyenne East | 10:00 am | Cheyenne | |
| Soph Boys Basketball @ Cheyenne East | 11:30 am | Cheyenne | |
| Varsity Boys Basketball @ Cheyenne East | 1:00 pm | Cheyenne | |
| Friday, February 14, 2020 |
| JV Boys Basketball vs South | 4:00 pm | Sheridan | |
| Soph Boys Basketball vs South | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs South | 7:00 pm | Sheridan | |
| Saturday, February 15, 2020 |
| JV Boys Basketball vs Laramie | 10:00 am | Sheridan | |
| Soph Boys Basketball vs Laramie | 11:30 am | Sheridan | |
| Varsity Boys Basketball vs Laramie | 1:00 pm | Sheridan | |
| Friday, February 21, 2020 |
| Soph Boys Basketball vs Campbell County | 4:00 pm | Sheridan | |
| JV Boys Basketball vs Campbell County | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs Campbell County | 7:00 pm | Sheridan | |
| Saturday, February 22, 2020 |
| Soph Boys Basketball @ Thunder Basin | 10:00 am | Gillette | |
| JV Boys Basketball @ Thunder Basin | 11:30 am | Gillette | |
| Varsity Boys Basketball @ Thunder Basin | 1:00 pm | Gillette | |
| Friday, February 28, 2020 |
| Soph Boys Basketball @ Natrona | 3:00 pm | Casper | |
| JV Boys Basketball @ Natrona | 4:30 pm | Casper | |
| Varsity Boys Basketball @ Natrona | 7:00 pm | Casper | |
| Thursday, March 5, 2020 to Saturday, March 7, 2020 |
| Varsity Boys Basketball @ Regionals | All Day | Thunder Basin | TBA |
| Thursday, March 12, 2020 to Saturday, March 14, 2020 |
| Varsity Boys Basketball @ State | All Day | Casper | TBA |
