| Monday, November 23, 2020 |
| Boys Basketball vs First Practice | 4:00 pm | SHS | All levels 1st Practice |
| Thursday, December 10, 2020 to Saturday, December 12, 2020 |
| JV Boys Basketball @ Strannigan | All Day | Riverton | |
| Soph Boys Basketball @ Strannigan | All Day | Riverton | |
| Varsity Boys Basketball @ Strannigan | All Day | Riverton | |
| Saturday, December 19, 2020 |
| JV Boys Basketball vs Cody | 12:00 pm | Sheridan | |
| Soph Boys Basketball vs Cody | 1:30 pm | Sheridan | |
| Varsity Boys Basketball vs Cody | 3:00 pm | Sheridan | |
| Thursday, January 7, 2021 |
| JV Boys Basketball vs Buffalo | 5:30 pm | | |
| Varsity Boys Basketball vs Buffalo | 7:00 pm | | |
| Friday, January 8, 2021 to Saturday, January 9, 2021 |
| Soph Boys Basketball @ Powder River Tourney | All Day | | Sundance/Moorcroft Tourney |
| Friday, January 8, 2021 |
| JV Boys Basketball vs BW (Billings Central) | 4:00 pm | Sheridan | Border War |
| Varsity Boys Basketball vs Border War | 7:00 pm | Sheridan | Border War |
| Saturday, January 9, 2021 |
| JV Boys Basketball vs BW (Laurel) | 10:00 am | Sheridan | Border War |
| Varsity Boys Basketball vs BW (Laurel) | 1:00 pm | Sherian | Border War |
| Friday, January 15, 2021 |
| 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, January 22, 2021 |
| JV Boys Basketball vs Campbell County | 4:00 pm | Sheridan | |
| Soph Boys Basketball vs Campbell County | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs Campbell County | 7:00 pm | Sheridan | |
| Saturday, January 23, 2021 |
| Soph Boys Basketball @ Thunder Basin | 10:00 am | Gillette | |
| JV Boys Basketball @ Thunder Basin | 11:30 am | Gillette | |
| Varsity Boys Basketball @ Thunder Basin | 2:30 pm | Gillette | |
| Friday, January 29, 2021 |
| Soph Boys Basketball @ Kelly Walsh | 3:00 pm | Casper | |
| JV Boys Basketball @ Kelly Walsh | 4:30 pm | Casper | |
| Varsity Boys Basketball @ Kelly Walsh | 7:30 pm | Casper | |
| Saturday, January 30, 2021 |
| Frosh Boys Basketball @ Buffalo | 11:00 am | Buffalo | |
| JV Boys Basketball @ Buffalo | 12:30 - 2:30 pm | | |
| Varsity Boys Basketball @ Buffalo | 2:00 pm | Buffalo | |
| Friday, February 5, 2021 |
| JV Boys Basketball vs Cheyenne Central | 4:00 pm | Sheridan | |
| Soph Boys Basketball vs Cheyenne Central | 5:30 pm | Sheridan | |
| Varsity Boys Basketball vs Cheyenne Central | 7:00 pm | Sheridan | |
| Saturday, February 6, 2021 |
| JV Boys Basketball vs Cheyenne East | 10:00 am | Sheridan | |
| Soph Boys Basketball vs Cheyenne East | 11:30 am | Sheridan | |
| Varsity Boys Basketball vs Cheyenne East | 1:00 pm | Sheridan | |
| Friday, February 12, 2021 |
| JV Boys Basketball @ Cheyenne South | 4:00 pm | Cheyenne | |
| Soph Boys Basketball @ Cheyenne South | 5:30 pm | Cheyenne | |
| Varsity Boys Basketball @ Cheyenne South | 7:00 pm | Cheyenne | |
| Saturday, February 13, 2021 |
| JV Boys Basketball @ Laramie | 10:00 am | Laramie | |
| Soph Boys Basketball @ Laramie | 11:30 am | Laramie | |
| Varsity Boys Basketball @ Laramie | 1:00 pm | Laramie | |
| Thursday, February 18, 2021 |
| JV Boys Basketball vs Thunder Basin | 3:30 pm | Sheridan | |
| Soph Boys Basketball vs Thunder Basin | 5:00 pm | Sheridan | |
| Varsity Boys Basketball vs Thunder Basin | 6:30 pm | Sheridan | |
| Friday, February 19, 2021 |
| Soph Boys Basketball @ Campbell County | 3:00 pm | Gillette | |
| JV Boys Basketball @ Campbell County | 4:30 pm | Gillette | |
| Varsity Boys Basketball @ Campbell County | 7:30 pm | Gillette | |
| Friday, February 26, 2021 |
| Soph Boys Basketball vs Kelly Walsh | 3:00 - 4:00 pm | Sheridan | |
| JV Boys Basketball vs Kelly Walsh | 4:30 - 6:30 pm | Sheridan | |
| Varsity Boys Basketball vs Kelly Walsh | 7:00 - 9:00 pm | Sheridan | |
| Thursday, March 4, 2021 to Saturday, March 6, 2021 |
| Varsity Boys Basketball @ Regionals | All Day | South | TBA |
| Thursday, March 11, 2021 to Saturday, March 13, 2021 |
| Varsity Boys Basketball @ State | All Day | Casper | TBA |
