Head to Head includes singles and doubles results.
| 01/23/20 | Craig Smart over Doug Wolleat | 6-2; 6-2 | Playoff Match |
| 01/14/20 | Craig Smart over Doug Wolleat | 6-0; 6-4 | |
| 12/03/19 | Doug Wolleat over Craig Smart |
6-2; 2-6; TB 10-3 |
|
| 07/01/19 | Craig Smart over Doug Wolleat | 6-1; 3-6; 6-3 | |
| 06/22/19 | Craig Smart over Doug Wolleat | 6-1; 6-0 | Playoff Match |
| 05/16/19 | Craig Smart over Doug Wolleat | 4-6; 6-2; 6-2 |
