Stadium: Court 1 Round: 24 Ground: Hardcourt indoor
| Challenger Champaign | 2019/11/14 19:25 | Lloyd Glasspool v Blaz Kavcic | 5-7,6-7 |
| Challenger Champaign | 2019/11/12 20:40 | Kaichi Uchida v Lloyd Glasspool | 5-7,6-7 |
| Challenger Champaign | 2019/11/11 18:15 | Lloyd Glasspool v Michael Geerts | 3-6,6-3,6-2 |
| Challenger Knoxville | 2019/11/06 16:30 | Lloyd Glasspool v Brandon Nakashima | 6-7,6-3,6-7 |
| Challenger Knoxville | 2019/11/04 15:00 | Lloyd Glasspool v Strong Kirchheimer | 1-6,5-7 |
| 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 Columbus 3 | 2019/09/16 21:15 | John McNally v Michael Geerts | 4-6,4-6 |
| Challenger New Haven | 2019/09/04 18:50 | John McNally v Marcos Giron | 6-7,6-7 |
| Challenger New Haven | 2019/09/03 16:35 | John McNally v Raymond Sarmiento | 3-6,7-6,6-4 |
| ATP Cincinnati | 2019/08/10 14:00 | John McNally v Federico Delbonis | 6-3,0-6,2-6 |
| Challenger Lexington | 2019/07/31 18:45 | John McNally v Maverick Banes | 6-7,6-3,1-6 |
| Challenger Lexington | 2019/07/29 23:00 | John McNally v Colin Sinclair | 7-6,3-6,6-1 |
| Challenger Binghamton | 2019/07/24 22:20 | Evgeny Karlovskiy v John McNally | 6-4,6-7,6-1 |
| Challenger Binghamton | 2019/07/23 22:35 | John McNally v Nathan Pasha | 7-6,6-4 |