Stadium: Court 12 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Champaign | 2023/07/20 16:50 | Winter, Edward v 베르날드, 알렉산더 | 4-6,2-6 |
| ITF M25 Champaign | 2023/07/19 22:20 | Winter, Edward v 바네르지, 사미르 | 6-3,7-5 |
| Dallas, Singles Main, M-ITF-USA-18A | 2023/07/15 19:00 | Winter, Edward v 마요, 아이단 | 4-6,4-6 |
| Dallas, Singles Main, M-ITF-USA-18A | 2023/07/14 18:35 | Winter, Edward v 샤흐터, 노아 | 6-1,6-0 |
| Dallas, Singles Main, M-ITF-USA-18A | 2023/07/13 15:30 | 돈스코이, 에브게니 v Winter, Edward | 2-6,4-6 |
| Dallas, Singles Main, M-ITF-USA-18A | 2023/07/12 16:30 | Valiev, Ilgiz v Winter, Edward | 0-6,3-6 |
| ITF M15 Irvine | 2023/07/01 18:50 | Winter, Edward v 반데카스틸, 퀸 | 6-4,4-6,0-6 |
| ITF M15 Irvine | 2023/06/30 21:00 | 데 존지, 다니엘 v Winter, Edward | 3-6,2-6 |
| ITF M15 Shanghai | 2023/07/11 07:15 | Sun, Qian v Jacob Bradshaw | 3-6,6-4,6-4 |
| ITF M15 Tianjin | 2023/07/05 04:40 | Jacob Bradshaw v Shin, Woobin | 4-6,4-6 |
| ITF M15 Tianjin | 2023/07/01 02:00 | 왕, 아우란 v Jacob Bradshaw | 6-4,0-6,6-4 |
| ITF M15 Tianjin | 2023/06/30 02:00 | 카스텔누오보, 루카 v Jacob Bradshaw | 6-7,2-6 |
| ITF M15 Tianjin | 2023/06/28 02:40 | 벤잘 알리아, 이그나시오 v Jacob Bradshaw | 2-6,4-6 |
| ITF M15 Tianjin | 2023/06/22 02:00 | 베크로프트, 이사크 v Jacob Bradshaw | 6-4,3-6,6-3 |
| ITF M15 Tianjin | 2023/06/21 05:05 | 탕, 성 v Jacob Bradshaw | 7-6,2-6,4-6 |
| ITF M25 Nakhon Si Thammarat | 2023/06/13 02:00 | Jacob Bradshaw v 트롱차로엔차이쿨, 위사야 | 3-6,7-6,5-7 |