Stadium: Court 2 Round: 26 Ground: Clay
| Challenger Tiburon | 2019/09/24 17:00 | Edan Leshem v Oliver Crawford | 6-7,6-4,6-4 |
| ITF M25 Houston | 2019/09/21 01:00 | Oliver Crawford v Hugo Gaston | 3-6,2-6 |
| ITF M25 Houston | 2019/09/20 00:00 | Ricardo Rodriguez-Pace v Oliver Crawford | 6-3,6-7,6-7 |
| ITF M25 Houston | 2019/09/18 23:45 | Sumit Sarkar v Oliver Crawford | 3-6,5-7 |
| Challenger Lexington | 2019/07/30 23:40 | Enzo Wallart v Oliver Crawford | 6-4,6-3 |
| ITF M25 Champaign | 2019/07/28 16:00 | Oliver Crawford v Jenson Brooksby | 2-6,1-6 |
| ITF M25 Champaign | 2019/07/27 19:00 | Liam Broady v Oliver Crawford | 6-3,4-6,2-6 |
| ITF M25 Champaign | 2019/07/26 20:30 | Oliver Crawford v Ruan Roelofse | 6-3,6-4 |
| ITF M15 Cancun | 2019/09/27 14:00 | Cristian Rodriguez v Taha Baadi | 6-2,7-5 |
| ITF M15 Cancun | 2019/09/26 16:00 | Cristian Rodriguez v Tyler Mercier | 6-4,6-3 |
| ITF M15 Cancun | 2019/09/25 14:30 | Cristian Rodriguez v Hillel Rousseau | 6-2,6-4 |
| ITF M15 Cancun | 2019/09/22 14:30 | Cristian Rodriguez v Adam El Mihdawy | 4-6,7-6,1-6 |
| ITF M15 Cancun | 2019/09/21 17:30 | Cristian Rodriguez v Peter Bertran | 6-1,6-0 |
| ITF M15 Cancun | 2019/09/20 14:00 | Tyler Mercier v Cristian Rodriguez | 3-6,5-7 |
| ITF M15 Cancun | 2019/09/19 16:30 | Aron Pierce v Cristian Rodriguez | 3-6,3-6 |
| ITF M15 Cancun | 2019/09/18 14:00 | Matt McBride v Cristian Rodriguez | 4-6,1-6 |