| Monday, December 2, 2019 |
| Boys Swimming 1st Practice | 4:00 pm | Pool | |
| Friday, December 13, 2019 |
| Boys Swimming @ Gillette Relays | 3:00 pm | Gillette | |
| Saturday, December 14, 2019 |
| Boys Swimming @ Gillette Pentathalon | 9:00 am | Gillette | |
| Tuesday, December 17, 2019 |
| Boys Swimming @ Buffalo (TB, CCHS) | 4:00 pm | Buffalo | |
| Friday, December 20, 2019 |
| Boys Swimming @ Green River Pre Invite | 4:00 pm | Green River | |
| Saturday, December 21, 2019 |
| Boys Swimming @ Green River Invite | 9:00 am | Green River | |
| Friday, January 10, 2020 |
| Boys Swimming vs Sheridan Pre-Invite | 4:00 pm | Sheridan | NC, East, KW |
| Saturday, January 11, 2020 |
| Boys Swimming vs Sheridan Invite | 9:00 am | Sheridan | NC, TB, CCHS, East, KW |
| Friday, January 17, 2020 |
| Boys Swimming @ Laramie | 5:00 pm | Laramie | |
| Saturday, January 18, 2020 |
| Boys Swimming @ Cheyenne Invite | 8:00 am | Cheyenne South | |
| Saturday, January 25, 2020 |
| Boys Swimming @ Gillette Dual Meet | 9:00 am | Gillette | not sure if can get in |
| Tuesday, January 28, 2020 |
| Boys Swimming vs TB, CCHS | 4:00 pm | Sheridan | |
| Friday, January 31, 2020 |
| Boys Swimming @ Laramie Invite | 8:00 am | Laramie | |
| Friday, February 7, 2020 to Saturday, February 8, 2020 |
| Boys Swimming @ Conference Meet | All Day | Gillette | |
| Friday, February 21, 2020 to Saturday, February 22, 2020 |
| Boys Swimming @ State Meet | All Day | Laramie | |
