Stadium: Court 8 Round: 54 Ground: Clay
| ITF - M15 Shymkent | 2021/04/05 05:00 | Oleg Syrovatskiy v Makhmudov, Damir | 7-5,6-1 |
| ITF - M15 Shymkent | 2021/04/06 05:50 | Jack Gibbens v Oleg Syrovatskiy | 6-1,6-3 |
| ITF - M15 Shymkent | 2021/04/05 05:00 | Oleg Syrovatskiy v Makhmudov, Damir | 7-5,6-1 |
| ITF - M15 Shymkent | 2021/04/05 05:00 | Oleg Syrovatskiy v Makhmudov, Damir | 7-5,6-1 |
| ITF M15 Nur-Sultan | 2021/02/08 06:00 | Makhmudov, Damir v Francesco Maestrelli | 0-6,2-6 |
| ITF M15 Nur-Sultan | 2021/02/01 05:00 | Shyla, Yaraslau v Makhmudov, Damir | 6-3,6-0 |
| Aktobe, Singles Qualifying M-ITF-KAZ-02A | 2020/02/17 04:55 | Federico Arnaboldi v Makhmudov, Damir | 6-3,6-2 |
| Aktobe, Singles Qualifying M-ITF-KAZ-02A | 2020/02/10 07:00 | Noskin, Egor v Makhmudov, Damir | 6-2,6-0 |
| Bukhara, Singles M-ITF-UZB-06A | 2019/10/14 08:10 | Rasamatov, Bekhzod v Makhmudov, Damir | 6-2,6-3 |
| Karshi, Singles Qualifying M-ITF-UZB-05A | 2019/10/07 05:00 | Noskin, Egor v Makhmudov, Damir | 6-2,6-1 |
| Almaty, Simples M-ITF-KAZ-09A | 2019/09/23 04:00 | Makhmudov, Damir v Ivan Zaytsev | 6-4,5-7,4-10 |