Stadium: Court 5 Round: 24 Ground: Hardcourt indoor
| ITF USA F33 | 2018/11/17 15:00 | Dragos Constantin Ignat v James Trotter | 6-2,6-7,6-1 |
| ITF Japan F8 | 2018/06/09 06:40 | Yunosuke Tanaka v James Trotter | 7-6,6-4 |
| ITF Japan F4 | 2018/03/25 01:00 | James Trotter v Shinta Fujii | 4-6,4-6 |
| ITF Japan F1 | 2018/03/04 01:00 | Rio Noguchi v James Trotter | 7-5,6-4 |
| ITF Japan F1 | 2018/03/03 01:00 | Kousuke Ogura v James Trotter | 3-6,3-6 |
| Challenger Kobe Qual | 2017/11/05 03:40 | James Trotter v Marinko Matosevic | 2-6,2-6 |
| Challenger Kobe Qual | 2017/11/04 02:00 | Yunseong Chung v James Trotter | 6-7,6-3,5-7 |
| ITF Japan F8 | 2017/06/11 00:00 | James Trotter v Kazuki Nishiwaki | 6-7,4-6 |
| Challenger Monterrey | 2019/04/01 22:45 | Roy Smith v Janko Tipsarevic | 6-7,4-6 |
| Challenger Drummondville | 2019/03/11 18:45 | Michael Redlicki v Roy Smith | 6-1,6-1 |
| Challenger Yokohama | 2019/02/25 02:30 | Kaichi Uchida v Roy Smith | 6-3,6-3 |
| ATP New York | 2019/02/10 21:20 | Ramkumar Ramanathan v Roy Smith | 4-6,6-2,6-4 |
| Challenger Cleveland | 2019/01/30 02:55 | Roy Smith v Donald Young | 6-4,0-6,7-6 |
| Challenger Cleveland | 2019/01/28 18:25 | Roy Smith v Gijs Brouwer | 7-6,6-3 |
| Challenger Newport Beach | 2019/01/21 19:30 | Roy Smith v Benjamin Bonzi | 2-6,5-7 |
| Challenger Canberra | 2019/01/07 04:15 | Tomas Barrios Vera v Roy Smith | 7-6,6-3 |