Stadium: Court 5 Round: 28 Ground: Hardcourt indoor
| Challenger Charlottesville | 2019/10/28 23:55 | Lloyd Glasspool v Alexander Ritschard | 4-6,4-6 |
| ITF M25 Fort Worth | 2019/10/22 19:05 | Tadeas Paroulek v Lloyd Glasspool | 6-4,6-3 |
| Challenger Las Vegas | 2019/10/15 21:25 | Lloyd Glasspool v Emilio Gomez | 2-6,7-6,3-6 |
| Challenger Las Vegas | 2019/10/14 18:00 | Lloyd Glasspool v Martin Redlicki | 7-5,7-6 |
| ITF M25 Norman | 2019/10/01 16:30 | Lloyd Glasspool v Jonathan Gray | 3-6,2-6 |
| Challenger Glasgow | 2019/09/17 14:05 | Lloyd Glasspool v Nicola Kuhn | 6-3,4-6,3-6 |
| 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 |
| ITF M25 Fayetteville | 2019/10/24 17:00 | Strong Kirchheimer v Aleksandar Kovacevic | 3-6,4-6 |
| ITF M25 Fayetteville | 2019/10/23 18:35 | Strong Kirchheimer v Timo Stodder | 7-5,6-2 |
| ITF M25 Waco | 2019/10/17 20:15 | Strong Kirchheimer v Ben Patael | 3-6,6-7 |
| Challenger Fairfield | 2019/10/07 21:05 | Evan King v Strong Kirchheimer | 6-7,6-3,6-4 |
| ITF M25 Norman | 2019/10/03 15:00 | Strong Kirchheimer v Sebastian Fanselow | 4-6,6-3,5-7 |
| ITF M25 Norman | 2019/10/01 17:20 | Andrew Watson v Strong Kirchheimer | 3-6,1-6 |
| Challenger Columbus 3 | 2019/09/17 22:00 | Strong Kirchheimer v Enzo Couacaud | 6-2,5-7,0-6 |
| Challenger Columbus 3 | 2019/09/16 17:35 | Robert Cash v Strong Kirchheimer | 3-6,4-6 |