Stadium: Centre Court Round: 24 Ground: Hardcourt indoor
| 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 Lexington | 2019/08/01 19:35 | Lloyd Glasspool v Sem Verbeek | 6-4,6-3 |
| Challenger Banja Luka | 2019/09/11 08:00 | Pedja Krstin v Riccardo Balzerani | 6-2,6-4 |
| Challenger Banja Luka | 2019/09/10 10:25 | Riccardo Balzerani v Michael Geerts | 7-6,6-1 |
| ITF M25 Trieste | 2019/09/04 10:10 | Riccardo Balzerani v Davide Galoppini | 5-7,5-7 |
| ITF M25 Trieste | 2019/09/03 11:35 | Khumoyun Sultanov v Riccardo Balzerani | 5-7,1-6 |
| Challenger Como | 2019/08/26 08:00 | Khumoyun Sultanov v Riccardo Balzerani | 6-3,7-6 |
| Challenger Cordenons | 2019/08/13 09:30 | Francesco Forti v Riccardo Balzerani | 6-4,4-6,6-2 |
| ITF M25 Appiano | 2019/08/11 09:00 | Christian Lindell v Riccardo Balzerani | 6-2,4-6,6-3 |
| ITF M25 Appiano | 2019/08/10 11:30 | Pietro Rondoni v Riccardo Balzerani | 1-6,4-6 |