Stadium: Court 3 Round: 25
| ITF M25 Tucson | 2019/01/08 19:05 | Mousheg Hovhannisyan v Siphosothando Montsi | 4-6,1-6 |
| ITF M25 Tucson | 2019/01/07 18:30 | Kento Tagashira v Siphosothando Montsi | 4-6,1-6 |
| ITF Zimbabwe F3 | 2018/06/11 07:00 | Niki Kaliyanda Poonacha v Siphosothando Montsi | 5-7,6-1,6-2 |
| ITF Zimbabwe F2 | 2018/06/05 07:00 | Matias Franco Descotte v Siphosothando Montsi | 6-3,6-3 |
| ITF Zimbabwe F1 | 2018/05/28 08:00 | Tukhula Jacobs v Siphosothando Montsi | 7-5,7-5 |
| ITF Egypt F12 | 2018/04/06 08:00 | Teymuraz Gabashvili v Siphosothando Montsi | 6-3,4-6,6-0 |
| ITF Egypt F12 | 2018/04/05 09:15 | Igor Marcondes v Siphosothando Montsi | 4-6,2-6 |
| ITF Egypt F12 | 2018/04/04 08:00 | Siphosothando Montsi v Mick Lescure | 4-6,6-3,7-6 |
| ITF M25 Los Angeles | 2019/01/02 22:10 | Lloyd Glasspool v Brandon Holt | 4-6,2-6 |
| Challenger Champaign | 2018/11/13 21:15 | Lloyd Glasspool v Reilly Opelka | 6-7,6-7 |
| Challenger Charlottesville | 2018/10/29 15:30 | Nuno Borges v Lloyd Glasspool | 3-6,6-7 |
| Challenger Charlottesville | 2018/10/28 17:50 | Henrik Wiersholm v Lloyd Glasspool | 4-6,2-6 |
| Challenger Charlottesville | 2018/10/27 21:45 | Lloyd Glasspool v Evan King | 1-6,6-3,6-2 |
| Challenger Las Vegas | 2018/10/21 19:15 | Lloyd Glasspool v Alexander Sarkissian | 4-6,4-6 |
| Challenger Las Vegas | 2018/10/20 22:00 | Lloyd Glasspool v Alen Avidzba | 7-5,6-3 |
| ITF Nigeria F4 | 2018/10/03 09:00 | Lloyd Glasspool v Skander Mansouri | 6-3,7-6 |