Stadium: Court 2 Round: 54 Ground: Hardcourt outdoor
| ITF M15 Irvine | 2023/06/29 00:10 | Gianni Ross v Maxwell McKennon | 1-6,3-6 |
| ITF M15 Los Angeles | 2023/06/21 19:50 | Nathan Ponwith v Maxwell McKennon | 6-4,6-4 |
| ITF M15 San Diego | 2023/06/05 19:00 | Bjorn Swenson v Maxwell McKennon | 1-6,4-6 |
| ITF M15 Rancho Santa Fe | 2023/05/30 16:00 | Noah Schachter v Maxwell McKennon | 6-0,7-6 |
| ITF M15 Rancho Santa Fe | 2023/05/29 20:30 | Alex Jones v Maxwell McKennon | 2-6,3-6 |
| Challenger Phoenix | 2023/03/13 22:40 | Alexander Shevchenko v Maxwell McKennon | 6-4,6-4 |
| ITF M25 Malibu | 2023/01/02 17:00 | Maxwell McKennon v Karlis Ozolins | 3-6,4-6 |
| UTR Pro Tennis Series California | 2022/12/23 01:48 | Alexander Kotzen v Maxwell McKennon | 6-3,6-1 |
| ITF M15 Lakewood | 2023/07/03 17:00 | Kyle Overmyer v Jelani Sarr | 5-7,6-4,10-6 |
| ITF M25 Mataro | 2023/05/22 10:30 | Stefanos Sakellaridis v Kyle Overmyer | 3-6,6-2,10-6 |
| ITF M25 Mataro | 2023/05/21 12:00 | Carlos Giraldi v Kyle Overmyer | 2-6,6-7 |
| ITF M25 Gurb | 2023/05/15 07:00 | Dali Blanch v Kyle Overmyer | 6-2,6-1 |
| ITF M25 Gurb | 2023/05/14 07:00 | Laurent Julia Calac v Kyle Overmyer | 2-6,4-6 |
| ITF M25 Valldoreix | 2023/05/07 14:30 | Kyle Overmyer v Xavi Matas Ortega | 2-6,1-6 |
| ITF M25 Santa Margherita | 2023/04/30 09:30 | Kyle Overmyer v Dimitris Sakellaridis | 6-7,7-6,5-10 |
| ITF M25 Santa Margherita | 2023/04/23 08:00 | Kyle Overmyer v Michele Ribecai | 4-6,6-3,2-10 |