| Sunday, August 9, 2020 |
| Tennis parent meeting | 5:30 - 6:30 pm | Tennis Courts | |
| Monday, August 10, 2020 |
| Tennis 1st Practice | 8:00 - 10:00 am | | 2nd practice will start at 4 pm |
| Tennis 2nd Practice | 4:00 pm | SHS | |
| Golf Parent Meeting | 5:30 pm | | |
| Saturday, August 15, 2020 to Saturday, August 15, 2020 |
| Tennis @ Casper | All Day | Casper | TBA |
| Thursday, August 20, 2020 |
| Tennis @ Jackson | 3:00 pm | Jackson | Results:  |
| Friday, August 21, 2020 |
| Tennis @ NC/KW | 10:00 - 1:00 pm | Casper | Results: |
| Saturday, August 22, 2020 |
| Tennis JV vs Campbell and Thunder basin | 9:00 - 12:00 pm | Sheridan | 9 am |
| Friday, August 28, 2020 |
| JV Tennis vs Powell/Cody | 10:00 - 2:00 pm | | Powell at 10, Cody at 3 pm |
| Tennis @ Cody/Powell | 10:00 - 2:00 pm | Cody | Results: |
| Saturday, August 29, 2020 |
| Tennis vs Torrington & Laramie | 12:00 - 3:00 pm | Sheridan | Results: |
| Friday, September 4, 2020 |
| Tennis vs East/Central | 8:00 - 12:00 pm | Sheridan | Central at 8 am, East at noon |
| Saturday, September 5, 2020 |
| Tennis vs South @ Natrona | 2:00 pm | Natrona County | |
| Saturday, September 12, 2020 |
| Tennis vs Gillette vs Thunder Basin/ Campbell County | 9:00 - 12:00 pm | Sheridan | Varsity Only TB @ 9, Campbell @ 12 |
| Tennis JV @ Campbell and Thunder | 9:00 am | Gillette | Thunder @ 9, Campbell @ 12 |
| Friday, September 18, 2020 to Saturday, September 19, 2020 |
| Tennis vs Conference Meet | All Day | Cody | |
| Thursday, September 24, 2020 to Saturday, September 26, 2020 |
| Tennis @ State Meet | All Day | Gillette | |
