Head to Head includes singles and doubles results.
| 11/04/23 | Ken Kroeger over Andrew Hebard | 7-5; 2-6; 7-5 | Playoff Match |
| 09/30/23 | Andrew Hebard over Ken Kroeger | 6-3; 6-3 | Doubles Match |
| 08/26/23 | Andrew Hebard over Ken Kroeger | 6-1; 6-4 | Doubles Match |
| 08/19/23 | Andrew Hebard over Ken Kroeger | 6-3; 6-4 | Doubles Match |
