Head to Head includes singles and doubles results.
| 06/01/21 | Jordan Shippee over Bill Cypert | 7-6; 7-6 | Playoff Match |
| 04/21/21 | Bill Cypert over Jordan Shippee | 6-2; 6-4 | |
| 03/30/21 | Jordan Shippee over Bill Cypert | 6-0; 3-6; 7-5 | |
| 03/25/21 | Bill Cypert over Jordan Shippee | 6-4; 6-4 |
