Stadium: Centre Court Round: 25 Ground: Hardcourt indoor
| Challenger Glasgow | 2019/09/16 15:10 | Lloyd Glasspool v Riccardo Balzerani | 6-3,6-2 |
| Challenger Cassis | 2019/09/02 08:30 | Lloyd Glasspool v Illya Marchenko | 4-6,4-6 |
| Challenger Vancouver | 2019/08/15 22:15 | Ricardas Berankis v Lloyd Glasspool | 7-6,6-1 |
| Challenger Vancouver | 2019/08/14 21:30 | Lloyd Glasspool v Taha Baadi | 6-3,6-2 |
| Challenger Vancouver | 2019/08/13 02:05 | Jordi Arconada v Lloyd Glasspool | 5-7,3-6 |
| Challenger Aptos | 2019/08/05 23:00 | Lloyd Glasspool v Martin Redlicki | 6-7,4-6 |
| Challenger Lexington | 2019/08/03 18:00 | Lloyd Glasspool v Alex Bolt | 3-6,2-6 |
| Challenger Lexington | 2019/08/02 15:00 | Lloyd Glasspool v Liam Broady | 6-4,6-3 |
| Challenger Istanbul | 2019/09/13 10:25 | Blaz Kavcic v Nicola Kuhn | 6-3,6-0 |
| Challenger Istanbul | 2019/09/12 07:00 | Nicola Kuhn v Ramkumar Ramanathan | 6-3,7-5 |
| Challenger Istanbul | 2019/09/10 07:00 | Nicola Kuhn v Victor Vlad Cornea | 6-2,6-4 |
| US Open | 2019/08/21 16:30 | Nicola Kuhn v Lukas Lacko | 4-6,6-7 |
| US Open | 2019/08/19 23:50 | Nicola Kuhn v Sergiy Stakhovsky | 6-4,6-4 |
| Challenger Segovia | 2019/08/04 16:00 | Pavel Kotov v Nicola Kuhn | 2-6,6-7 |
| Challenger Segovia | 2019/08/03 15:55 | Nicola Kuhn v Markus Eriksson | 6-2,6-2 |
| Challenger Segovia | 2019/08/02 16:45 | Nicola Kuhn v Altug Celikbilek | 7-5,6-4 |