| Monday, November 30, 2020 |
| Boys Swimming 1st Practice | 4:00 pm | Pool | |
| Friday, December 11, 2020 |
| Boys Swimming @ Laramie Relays | 3:00 - 6:00 pm | Gillette | |
| Saturday, December 12, 2020 |
| Boys Swimming @ Laramie Pentathalon | 9:00 - 3:00 pm | Gillette | |
| Tuesday, December 15, 2020 |
| Boys Swimming vs Buffalo | 4:00 - 6:00 pm | Sheridan | |
| 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 Pre-Invite | 4:00 - 6:00 pm | Sheridan | NC East, Central |
| Saturday, January 9, 2021 |
| Boys Swimming vs Sheridan Invite | 9:00 - 10:00 am | Sheridan | Lar, TB, CCHS, NC, East, Central, |
| Friday, January 15, 2021 |
| Boys Swimming @ SE Duals | 5:00 - 7:00 pm | Laramie or Cheyenne | |
| Saturday, January 16, 2021 |
| Boys Swimming @ SE Duals | 8:00 - 3:00 pm | Cheyenne or Laramie | |
| Tuesday, January 19, 2021 |
| Boys Swimming vs Kelly Walsh | 4:00 - 6:00 pm | Sheridan | KW |
| Saturday, January 30, 2021 |
| Boys Swimming @ Gillette Invite | 8:00 - 3:00 pm | Gillette | |
| Friday, February 5, 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 | |
