Head to Head includes singles and doubles results.
| 05/31/23 | Riley Smith over Matteo Boffo | 6-4; 6-3 | Playoff Match |
| 05/09/23 | Riley Smith over Matteo Boffo | 6-4; 7-5 | |
| 04/05/23 | Riley Smith over Matteo Boffo | 7-5; 6-2 | |
| 08/13/22 | Matteo Boffo over Riley Smith | 4-6; 6-0; 6-3 | |
| 08/05/22 | Matteo Boffo over Riley Smith | 6-4; 6-4 |
