Stadium: Court 22 Round: 54 Ground: Hardcourt outdoor
| 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 |
| ITF M15 Heraklion | 2019/05/22 06:55 | James Story v Milen Ianakiev | 3-6,4-6 |
| ITF M15 Heraklion | 2019/05/20 13:00 | Milen Ianakiev v Alexandros Roumpis | 6-4,6-2 |
| ITF M15 Heraklion | 2019/05/20 07:00 | Milen Ianakiev v George Davies | 6-4,6-3 |
| ITF M25 Roehampton | 2019/07/29 12:15 | Marcus Walters v Sizya Ernest Kivanda | 6-1,6-1 |
| ITF M25 Porto | 2019/07/22 15:00 | Sizya Ernest Kivanda v Diogo Marques | 2-6,6-3,7-10 |
| ITF M25 Bakio | 2019/07/01 10:20 | Sizya Ernest Kivanda v Inigo T Martin | 1-6,3-6 |
| ITF M25 Palma del Rio | 2019/06/24 07:30 | Sizya Ernest Kivanda v Juan P Canas Garcia | 3-6,1-6 |
| ITF M15 Sozopol | 2019/05/07 09:00 | Sizya Ernest Kivanda v Llewelyn Bevan | 6-7,6-4,7-10 |
| ITF M15 Sozopol | 2019/05/06 07:00 | Sizya Ernest Kivanda v Radoslav Shandarov | 6-3,2-6,10-6 |
| ITF M25 Sunderland | 2019/04/08 09:40 | Robert Carter v Sizya Ernest Kivanda | 6-4,7-5 |
| ITF M25 Bakersfield | 2019/03/11 17:00 | Abraham Asaba v Sizya Ernest Kivanda | 6-3,6-4 |