| Bulgarian Int. Qual | 2022/10/06 08:10 | Papadopoulos, Dimitrios v Dimitrov, Ivan | L | 2-1 |
| Bulgarian Int Qual | 2021/10/07 10:35 | Yusuf Yasar v Dimitrov, Ivan | L | 2-0 |
| Bulgarian Int. | 2020/10/02 16:00 | Borko Petrovic v Dimitrov, Ivan | L | 2-0 |
| Bulgarian Int. | 2020/10/02 09:00 | Ivan Pejoski v Dimitrov, Ivan | W | 0-2 |
| Bulgarian Int. Qual | 2019/10/03 08:20 | Borko Petrovic v Dimitrov, Ivan | L | 2-0 |
| Latvia Int. Qual | 2023/08/31 06:40 | Crowley, Tony v Christian Tomic | L | 0-2 |
| Nouvelle Aquitane Future Series Qual | 2023/07/06 07:00 | Noguera, Juan v Crowley, Tony | L | 2-0 |
| Croatia Open | 2022/06/20 13:35 | Eliel Melleri v Crowley, Tony | L | 2-0 |
| Irish Open Qual | 2019/11/13 11:35 | Wolfgang Gnedt v Crowley, Tony | L | 2-0 |
| Latvia Int. Qual | 2019/05/30 06:30 | Crowley, Tony v Boman, Marcus | L | 0-2 |