Stadium: Centre Court Round: 25 Ground: Hardcourt indoor
| Challenger Nottingham | 2019/06/10 13:35 | Brydan Klein v Lloyd Glasspool | 7-6,6-2 |
| Challenger Surbiton | 2019/06/03 14:30 | Lloyd Glasspool v Dominik Koepfer | 4-6,6-7 |
| ITF M15 Heraklion | 2019/05/19 07:30 | Lloyd Glasspool v Yshai Oliel | 3-6,4-6 |
| ITF M15 Heraklion | 2019/05/18 07:30 | Lloyd Glasspool v Peter Bothwell | 6-7,6-4,6-1 |
| ITF M15 Heraklion | 2019/05/17 07:00 | Lloyd Glasspool v Aaron Addison | 6-3,6-2 |
| ITF M15 Heraklion | 2019/05/16 07:00 | Lloyd Glasspool v Erik Crepaldi | 6-1,6-1 |
| ITF M15 Heraklion | 2019/05/15 09:35 | Lloyd Glasspool v Samuel Bothwell | 6-3,6-4 |
| ITF M15 Heraklion | 2019/05/10 07:00 | Lloyd Glasspool v Jonas Trinker | 4-6,4-6 |
| Challenger Braunschweig | 2019/07/08 11:00 | Nicola Kuhn v Mats Moraing | 3-6,6-2,5-7 |
| Challenger Ludwigshafen | 2019/07/03 13:00 | Nicola Kuhn v Andrej Martin | 5-7,6-4,3-6 |
| Challenger Ludwigshafen | 2019/07/02 16:00 | Gianluigi Quinzi v Nicola Kuhn | 6-3,6-7,3-6 |
| Challenger Shymkent 2 | 2019/06/14 05:00 | Nicola Kuhn v Stefano Travaglia | 2-6,2-6 |
| Challenger Shymkent 2 | 2019/06/13 05:50 | Riccardo Bonadio v Nicola Kuhn | 6-4,4-6,4-6 |
| Challenger Shymkent 2 | 2019/06/11 08:15 | Nicola Kuhn v Akira Santillan | 1-6,7-5,6-3 |
| Challenger Shymkent 2 | 2019/06/10 06:30 | Roman Safiullin v Nicola Kuhn | 6-3,2-6,2-6 |
| Challenger Almaty | 2019/06/06 06:15 | Nicola Kuhn v Alejandro Tabilo | 0-6,6-7 |