| Monday, November 30, 2020 |
| Boys Swimming 1st Practice | 4:00 pm | Pool | |
| Friday, December 11, 2020 |
| Boys Swimming @ Gillette Relays | 3:00 - 6:00 pm | Gillette | |
| Saturday, December 12, 2020 |
| Boys Swimming @ Gillette Pentathalon | 9:00 - 3:00 pm | Gillette | |
| Tuesday, December 15, 2020 |
| Boys Swimming vs Buffalo/Thunder/Campbell Cty | 4:00 - 6:00 pm | Sheridan | Buffalo, Thunder, Campbell Ct |
| Friday, December 18, 2020 |
| Boys Swimming @ Green River Pre Invite | 4:00 - 6:00 pm | Green River | |
| Saturday, December 19, 2020 |
| Boys Swimming @ Green River Invite | 9:00 - 4:00 pm | Green River | |
| Friday, January 8, 2021 |
| Boys Swimming vs Sheridan Friday Invite | 4:00 - 6:00 pm | Sheridan | NC, East, Buffalo |
| Saturday, January 9, 2021 |
| Boys Swimming vs Saturday Sheridan Invite | 10:00 am | Sheridan | Laramie, KW, East |
| Friday, January 15, 2021 |
| Boys Swimming @ SE Duals | 5:00 pm | Cheyenne South | |
| Saturday, January 16, 2021 |
| Boys Swimming @ SE Duals | 8:00 am | Laramie | |
| Tuesday, January 19, 2021 |
| Boys Swimming vs Kelly Walsh | 4:00 - 6:00 pm | Sheridan | KW |
| Friday, January 22, 2021 |
| Boys Swimming vs Newcastle | 4:00 pm | | |
| Friday, January 29, 2021 to Saturday, January 30, 2021 |
| Boys Swimming @ Cheyenne/Laramie TBD | All Day | | |
| Saturday, February 6, 2021 to Saturday, February 6, 2021 |
| Boys Swimming @ Conference Meet | All Day | Gillette | |
| Thursday, February 18, 2021 to Friday, February 19, 2021 |
| Boys Swimming @ State Meet | All Day | Gillette | |
