Stadium: Court 7 Round: 54 Ground: Hardcourt outdoor
| ITF M25 Malibu | 2019/11/04 18:00 | Drew Baird v Goncalo Ferreira | 3-6,6-1,10-8 |
| ITF M15 Champaign | 2019/09/10 18:00 | Drew Baird v Tom Fawcett | 4-6,6-7 |
| ITF M15 Pittsburgh | 2019/07/04 14:00 | Drew Baird v Alexander Cozbinov | 1-6,1-6 |
| ITF M15 Pittsburgh | 2019/07/03 14:00 | Strong Kirchheimer v Drew Baird | 6-7,6-1,1-6 |
| ITF M15 Rochester | 2019/06/27 19:45 | Drew Baird v Ricardo Rodriguez-Pace | 2-6,3-6 |
| ITF M15 Rochester | 2019/06/26 22:30 | Drew Baird v Jack Mingjie Lin | 6-3,6-1 |
| ITF M15 Orlando | 2019/06/20 13:00 | Drew Baird v Alan Kohen | 5-7,6-3,6-7 |
| ITF M15 Orlando | 2019/06/19 16:55 | Marcus McDaniel v Drew Baird | 5-7,3-6 |
| ITF M25 Malibu | 2019/11/04 18:00 | Chris Wettengel v Milen Ianakiev | 6-2,3-6,3-10 |
| ITF M25 Claremont | 2019/10/07 18:00 | Milen Ianakiev v Diego Nava | 6-4,3-6,8-10 |
| ITF M25 Chiswick | 2019/08/05 14:10 | Milen Ianakiev v Sizya Ernest Kivanda | 2-6,4-6 |
| ITF M25 Roehampton | 2019/07/29 08:30 | Milen Ianakiev v Sacha Modica | 4-6,2-6 |
| ITF M15 Plovdiv | 2019/06/04 06:30 | Milen Ianakiev v Andrea Bessire | 4-6,2-6 |
| ITF M15 Plovdiv | 2019/06/03 10:00 | Milen Ianakiev v Cosmin Ontica | 1-6,6-4,10-6 |
| ITF M15 Heraklion | 2019/05/28 09:00 | Omni Kumar v Milen Ianakiev | 6-3,7-5 |
| ITF M15 Heraklion | 2019/05/23 08:50 | Andres Artunedo Martinavarr v Milen Ianakiev | 6-3,6-4 |