Stadium: Court 1 Round: 25 Ground: Clay
| Challenger Cleveland | 2024/01/30 15:00 | Sebastian Fanselow v William Grant | 7-6,6-1 |
| Challenger Cleveland | 2024/01/29 16:45 | William Grant v Vishwa Aduru | 2-6,6-4,6-1 |
| Challenger Cleveland | 2024/01/28 20:05 | Alafia Ayeni v William Grant | 1-6,6-1,2-6 |
| ITF M25 Wesley Chapel | 2024/01/23 17:15 | Roberto Cid Subervi v William Grant | 6-0,6-2 |
| UTR Pro Florida | 2023/12/11 21:40 | William Grant v Spencer Gray | 6-7,6-4,6-7 |
| UTR Pro Florida | 2023/12/10 21:21 | William Grant v Chen Dong | 7-6,6-2 |
| ITF M15 East Lansing | 2023/11/18 15:55 | Samir Banerjee v William Grant | 6-2,6-2 |
| ITF M15 East Lansing | 2023/11/17 16:00 | Arda Azkara v William Grant | 4-6,0-6 |
| ITF M15 Sunrise | 2024/02/06 15:00 | Kyle Overmyer v Marko Stakusic | 6-4,6-1 |
| ITF M25 Wesley Chapel | 2024/01/25 14:45 | Nick Chappell v Kyle Overmyer | 6-3,6-1 |
| ITF M25 Wesley Chapel | 2024/01/24 17:00 | Jake Van Emburgh v Kyle Overmyer | 5-7,3-6 |
| ITF M25 Wesley Chapel | 2024/01/23 13:45 | Kyle Overmyer v Matthew Segura | 6-3,6-0 |
| ITF M25 Wesley Chapel | 2024/01/22 14:00 | Johannes Ingildsen v Kyle Overmyer | 2-6,6-2,8-10 |
| ITF M25 Ithaca | 2024/01/15 15:00 | Bryce Nakashima v Kyle Overmyer | 6-3,6-2 |
| ITF M15 Boca Raton | 2023/11/13 14:00 | Alvin N Tudorica v Kyle Overmyer | 6-3,7-5 |
| ITF M25 Austin | 2023/11/06 16:00 | Kyle Overmyer v Lorenzo Esquici | 3-6,3-6 |