Stadium: Court 5 Round: 26 Ground: Hardcourt indoor
| Challenger Champaign | 2019/11/12 20:40 | Kaichi Uchida v Glasspool, Lloyd | 5-7,6-7 |
| Challenger Champaign | 2019/11/11 18:15 | Glasspool, Lloyd v Michael Geerts | 3-6,6-3,6-2 |
| Challenger Knoxville | 2019/11/06 16:30 | Glasspool, Lloyd v Brandon Nakashima | 6-7,6-3,6-7 |
| Challenger Knoxville | 2019/11/04 15:00 | Glasspool, Lloyd v Strong Kirchheimer | 1-6,5-7 |
| Challenger Charlottesville | 2019/10/28 23:55 | Glasspool, Lloyd v Alexander Ritschard | 4-6,4-6 |
| Fort Worth, Singles Qualifying M-ITF-USA-42A | 2019/10/22 19:05 | Paroulek, Tadeas v Glasspool, Lloyd | 6-4,6-3 |
| Challenger Las Vegas | 2019/10/15 21:25 | Glasspool, Lloyd v Emilio Gomez | 2-6,7-6,3-6 |
| Challenger Las Vegas | 2019/10/14 18:00 | Glasspool, Lloyd v Redlicki, Martin | 7-5,7-6 |
| Challenger Champaign | 2019/11/12 19:40 | Kavcic, Blaz v Francisco Cerundolo | 6-2,6-0 |
| Challenger Champaign | 2019/11/11 18:20 | Ryan Peniston v Kavcic, Blaz | 4-6,3-6 |
| Challenger Knoxville | 2019/11/05 19:45 | Kavcic, Blaz v Edan Leshem | 2-6,6-7 |
| Challenger Charlottesville | 2019/10/29 22:50 | Kavcic, Blaz v Vasek Pospisil | 6-7,4-6 |
| Challenger Charlottesville | 2019/10/28 20:45 | Young, Donald v Kavcic, Blaz | 3-6,6-7 |
| Brest, France | 2019/10/22 14:45 | Kavcic, Blaz v Antoine Hoang | 6-2,1-6,2-6 |
| Brest, France | 2019/10/21 14:50 | Alexandre Muller v Kavcic, Blaz | 6-7,6-7 |
| Challenger - Barcelone | 2019/10/02 11:00 | Federico Gaio v Kavcic, Blaz | 6-1,6-0 |