Stadium: Court 8 Round: 26 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 - Irvine | 2023/06/28 20:00 | ZhengQing Ji v Edward Winter | 4-6,6-7 |
| ITF M15 - South Bend | 2023/06/23 15:00 | Axel Nefve v Edward Winter | 6-4,6-1 |
| ITF M15 - South Bend | 2023/06/22 15:00 | Adhithya Ganesan v Edward Winter | 4-6,3-6 |
| ITF M15 - South Bend | 2023/06/21 15:00 | Benjamin Thomas George v Edward Winter | 6-4,0-6,6-7 |
| ITF M25 - Wichita | 2023/06/14 15:00 | Edward Winter v Axel Nefve | 3-6,2-6 |
| ITF M15 - Rancho Santa Fe | 2023/06/01 19:20 | Edward Winter v Jack Anthrop | 3-6,2-6 |
| ITF M15 - Rancho Santa Fe | 2023/05/30 19:00 | Edward Winter v Hudson Rivera | 6-3,6-7,6-0 |
| ITF M15 - Tacarigua | 2023/04/26 14:00 | Edward Winter v Evan Bynoe | 2-6,2-6 |