Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Houston | 2019/11/11 18:50 | Liam Caruana v Mohamed Abdel-Aziz | 6-2,6-4 |
| Challenger Charlottesville | 2019/10/31 20:10 | Liam Caruana v Blaz Rola | 3-6,2-6 |
| Challenger Charlottesville | 2019/10/30 16:10 | Gianni Ross v Liam Caruana | 6-7,1-6 |
| Challenger Charlottesville | 2019/10/29 14:00 | Roy Smith v Liam Caruana | 4-6,5-7 |
| Challenger Charlottesville | 2019/10/28 14:00 | Liam Caruana v Cannon Kingsley | 6-3,7-6 |
| ITF M25 Fayetteville | 2019/10/23 18:00 | Nick Chappell v Liam Caruana | 7-5,6-4 |
| ITF M25 Waco | 2019/10/17 16:00 | Nick Chappell v Liam Caruana | 6-4,6-4 |
| ITF M25 Waco | 2019/10/16 14:45 | Liam Caruana v Zachary Svajda | 6-3,6-3 |
| Challenger Charlottesville | 2019/10/29 22:05 | Filip Peliwo v Ivo Karlovic | 6-1,7-5 |
| ATP Basel | 2019/10/19 12:00 | Peter Gojowczyk v Ivo Karlovic | 6-2,6-4 |
| ATP Moscow | 2019/10/17 19:40 | Marin Cilic v Ivo Karlovic | 6-1,7-6 |
| ATP Moscow | 2019/10/15 14:10 | Ivo Karlovic v Aljaz Bedene | 6-4,6-7,7-6 |
| ATP Cincinnati | 2019/08/12 19:35 | Ivo Karlovic v Jan-Lennard Struff | 5-7,6-7 |
| ATP Cincinnati | 2019/08/11 18:30 | Philipp Kohlschreiber v Ivo Karlovic | 6-7,7-6,4-6 |
| ATP Cincinnati | 2019/08/10 20:10 | Ivo Karlovic v Tennys Sandgren | 4-6,6-4,7-6 |
| ATP Montreal | 2019/08/03 16:30 | Evgeny Donskoy v Ivo Karlovic | 4-6,6-4,6-7 |