Stadium: Court 1 Round: 27 Ground: Clay
| ITF USA F26 | 2018/09/28 18:50 | Paul Oosterbaan v Strong Kirchheimer | 2-6,3-6 |
| ITF M15 Orlando | 2019/06/20 15:25 | Strong Kirchheimer v Logan Zapp | 6-2,6-1 |
| ITF M15 Orlando | 2019/06/19 13:00 | Strong Kirchheimer v Alexander Knight | 6-2,6-4 |
| ITF M25 Wichita | 2019/06/12 19:45 | Martin Redlicki v Strong Kirchheimer | 6-3,4-6,7-5 |
| ITF M15 Champaign | 2019/06/09 17:00 | Strong Kirchheimer v Nathan Ponwith | 6-7,4-6 |
| ITF M15 Champaign | 2019/06/08 17:00 | Strong Kirchheimer v Diego Hidalgo | 5-7,6-3,6-3 |
| ITF M15 Champaign | 2019/06/07 18:40 | Tom Fawcett v Strong Kirchheimer | 3-6,4-6 |
| ITF M15 Champaign | 2019/06/06 17:00 | Herbert Jody Maginley v Strong Kirchheimer | 6-7,3-6 |
| ITF M15 Champaign | 2019/06/05 17:00 | Luke Jacob Gamble v Strong Kirchheimer | 3-6,3-6 |
| ITF M15 Orlando | 2019/06/20 16:00 | George Botezan v Paul Oosterbaan | 6-3,5-7,6-7 |
| ITF M15 Orlando | 2019/06/19 15:40 | Michael Shabaz v Paul Oosterbaan | 4-6,7-6,3-6 |
| ITF M15 Cancun | 2019/06/05 13:30 | Austin Rapp v Paul Oosterbaan | 3-6,6-4,7-5 |
| ITF M15 Cancun | 2019/05/28 13:30 | Paul Oosterbaan v Alejandro Gomez | 2-6,6-4,3-6 |
| ITF M25 Pensacola | 2019/05/09 15:00 | Alejandro Gomez v Paul Oosterbaan | 6-2,7-6 |
| ITF M25 Pensacola | 2019/05/08 14:00 | Grey Hamilton v Paul Oosterbaan | 6-7,1-6 |
| ITF M25 Vero Beach | 2019/05/04 16:00 | Dmitry Popko v Paul Oosterbaan | 6-2,6-1 |
| ITF M25 Vero Beach | 2019/05/02 14:00 | Andrew Watson v Paul Oosterbaan | 4-6,3-6 |