| Challenger Portoroz MD | 08/10 20:05 | 28 | P-Castillo/Vasilevski v Berrettini/Cipolla | 6-3,6-4 | |
| Challenger Portoroz MD | 08/09 15:45 | 27 | P-Castillo/Vasilevski v F Delgado/K-Desman | 6-0,6-0 | |
| Challenger Portoroz MD | 08/08 17:35 | 26 | Podlipnik-Castillo/Vasilevski v Kovalik/Tsitsipas | 7-6,6-2 | |
| ATP Kitzbuhel MD | 08/05 09:30 | 29 | Cuevas/Duran v Podlipnik-Castillo/Vasilevski | 6-4,4-6,12-10 | |
| ATP Kitzbuhel MD | 08/04 15:15 | 28 | Knowle/Middelkoop v Podlipnik-Castillo/Vasilevski | 5-7,6-3,7-10 | |
| ATP Kitzbuhel MD | 08/03 11:30 | 27 | Podlipnik-Castillo/Vasilevski v Peralta/Zeballos | 3-6,6-3,10-8 | |
| ATP Kitzbuhel MD | 07/31 13:35 | 26 | Dutra Silva/Lorenzi v P-Castillo/Vasilevski | 3-6,2-6 | |
| ATP Gstaad MD | 07/27 09:30 | 27 | Podlipnik-Castillo/Vasilevski v Jebavy/Middelkoop | 6-2,3-6,8-10 | |
| ATP Gstaad MD | 07/26 08:30 | 26 | P-Castillo/Vasilevski v Bagnis/Daniel | 6-2,6-2 | |
| ATP Bastad MD | 07/19 14:00 | 26 | Ymer/Ymer v Podlipnik-Castillo/Vasilevski | 6-4,6-3 | |
| Wimbledon MD | 07/11 13:45 | 27 | Podlipnik-Castillo/Vasilevski v Mektic/Skugor | 7-6,4-6,6-7,5-7 | |
| Wimbledon MD | 07/10 10:30 | 26 | Klaasen/Ram v Podlipnik-Castillo/Vasilevski | 4-6,6-7,3-6 | |
| Wimbledon MD | 07/07 12:00 | 25 | Podlipnik-Castillo/Vasilevski v Cabal/Farah | Retired | |
| Wimbledon MD | 07/05 13:45 | 24 | Lipsky/Tiafoe v Podlipnik-Castillo/Vasilevski | 4-6,5-7,7-5,2-6 | |
| Challenger Ilkley MD | 06/21 11:00 | 27 | Paes/Shamasdin v P-Castillo/Vasilevski | 7-6,6-2 | |
| Challenger Ilkley MD | 06/19 16:30 | 26 | Galdos/Nedunchezhiyan v Podlipnik-Castillo/Vasilevski | 6-7,6-7 | |
| Challenger Caltanissetta MD | 06/14 16:25 | 27 | P-Castillo/Vasilevski v Bagnis/Cecchinato | 2-6,6-2,11-13 | |
| Challenger Caltanissetta MD | 06/12 13:50 | 26 | Podlipnik-Castillo/Vasilevski v Chaplin/Sandgren | 7-5,6-2 | |
| Challenger Shymkent MD | 05/26 05:00 | 29 | Podlipnik-Castillo/Vasilevski v Geens/Paz | 6-4,6-2 | |
| Challenger Shymkent MD | 05/24 10:05 | 27 | Podlipnik-Castillo/Vasilevski v Golubev/Nedovyesov | 6-2,7-6 | |
| Challenger Samarkand MD | 05/18 13:00 | 28 | P-Castillo/Vasilevski v Gunneswaran/Vardhan | 6-7,6-3,2-10 | |
| Challenger Samarkand MD | 05/17 05:00 | 27 | Podlipnik-Castillo/Vasilevski v Betov/Shyla | 6-1,6-4 | |
| Challenger Karshi MD | 05/11 08:40 | 28 | P-Castillo/Vasilevski v Krawietz/M-Maceiras | 6-7,7-6,2-10 | |
| Challenger Karshi MD | 05/10 09:30 | 27 | Podlipnik-Castillo/Vasilevski v Karatsev/Setkic | 4-6,6-3,13-11 | |
| Challenger Karshi MD | 05/09 10:15 | 26 | Podlipnik-Castillo/Vasilevski v Matsui/Ramanathan | 7-6,6-3 | |
| ATP Istanbul MD | 05/04 12:30 | 27 | P-Castillo/Vasilevski v Smith/Thompson | 3-6,1-6 | |
| ATP Istanbul MD | 05/03 17:00 | 26 | Celikbilek/Ilkel v P-Castillo/Vasilevski | 3-6,5-7 | |
| Challenger Anning MD | 04/29 03:30 | 28 | Podlipnik-Castillo/Vasilevski v De Waard/Kavcic | 6-2,4-6,8-10 | |
| Challenger Anning MD | 04/29 03:25 | - | P-Castillo/Vasilevski v De Waard/Kavcic | 6-2,4-6,0-0 | |
| Challenger Anning MD | 04/27 10:05 | 27 | Bai/Wu v Podlipnik-Castillo/Vasilevski | 6-7,7-6,5-10 |