Head to Head includes singles and doubles results.
| 04/26/24 | Dan Ostberg over John Shea | 6-2; 6-2 | |
| 04/27/24 | Dan Ostberg over John Shea | 6-0; 6-0 | |
| 10/10/23 | Dan Ostberg over John Shea | 7-5; 6-3 | Playoff Match |
| 09/10/23 | Dan Ostberg over John Shea | 6-4; 7-6 |
