| US Open MD | 08/31 15:00 | 24 | Tsitsipas/Tsitsipas v Reyes-Varela/Vega Hernandez | 7-6,6-4 | |
| Wimbledon MD | 07/07 18:30 | 24 | Tsitsipas/Tsitsipas v Fils/Van Assche | 7-6,4-6,2-6 | |
| The Boodles | 07/01 15:00 | - | Tsitsipas/Tsitsipas v Cash/Johnson | 6-7,6-4,1-0 | |
| French Open MD | 05/30 12:40 | 24 | Tsitsipas/Tsitsipas v Arevalo/Rojer | 3-6,6-3,6-7 | |
| ATP Madrid MD | 04/28 17:20 | 25 | Tsitsipas/Tsitsipas v Arevalo/Rojer | 6-7,5-7 | |
| ATP Monte Carlo MD | 04/12 11:50 | 26 | Tsitsipas/Tsitsipas v Arevalo/Rojer | 2-6,7-6,5-10 | |
| ATP Monte Carlo MD | 04/10 12:30 | 25 | Tsitsipas/Tsitsipas v Dimitrov/Hurkacz | 7-6,6-7,10-5 | |
| ATP Rotterdam MD | 02/13 10:00 | 26 | Glasspool/Heliovaara v Tsitsipas/Tsitsipas | 6-3,6-4 | |
| Davis Cup | 02/05 10:00 | 45 | Tsitsipas/Tsitsipas v Escobar/Hidalgo | Cancelled | |
| Australian Open MD | 01/21 01:30 | 25 | Koolhof/Skupski v Tsitsipas/Tsitsipas | 7-6,4-6,7-6 | |
| Australian Open MD | 01/19 04:30 | 24 | Ramanathan/Reyes-Varela v Tsitsipas/Tsitsipas | 6-3,5-7,3-6 | |
| US Open MD | 09/01 21:30 | 24 | Eubanks/Shelton v Tsitsipas/Tsitsipas | 3-6,7-6,6-2 | |
| ATP Mallorca MD | 06/21 13:00 | 26 | Arevalo/Rojer v Tsitsipas/Tsitsipas | 6-3,6-4 | |
| ATP Stuttgart MD | 06/08 13:00 | 27 | Tsitsipas/Tsitsipas v Hurkacz/Pavic | 6-4,6-7,5-10 | |
| ATP Stuttgart MD | 06/07 15:30 | 26 | Goransson/Mclachlan v Tsitsipas/Tsitsipas | 6-7,7-6,8-10 | |
| ATP Madrid MD | 05/03 10:00 | 25 | Murray/Venus v Tsitsipas/Tsitsipas | 6-2,3-6,10-7 | |
| ATP Monte Carlo MD | 04/13 15:25 | 26 | Tsitsipas/Tsitsipas v Mektic/Pavic | 3-6,3-6 | |
| ATP Monte Carlo MD | 04/11 13:25 | 25 | Tsitsipas/Tsitsipas v Golubev/Sonego | 6-7,6-4,10-2 | |
| ITF M15 Heraklion MD | 11/30 13:20 | 26 | Tsitsipas/Tsitsipas v Kountourakis/Skorilas | 2-6,4-6 | |
| ITF M15 Heraklion MD | 11/19 12:40 | 28 | Bergevi/Wehnelt v Tsitsipas/Tsitsipas | 6-4,6-4 | |
| ITF M15 Heraklion MD | 11/18 12:00 | 27 | Handel/Schaer v Tsitsipas/Tsitsipas | Walkover | |
| ATP Hamburg MD | 07/13 15:25 | 26 | Tsitsipas/Tsitsipas v Puetz/Venus | 5-7,6-7 | |
| Wimbledon MD | 07/02 13:30 | 24 | Tsitsipas/Tsitsipas v Munar/Norrie | 5-7,6-7 | |
| ATP Halle MD | 06/15 09:00 | 25 | Demoliner/Gonzalez v Tsitsipas/Tsitsipas | Cancelled | |
| ATP Lyon MD | 05/19 10:45 | 26 | Ebden/Smith v Tsitsipas/Tsitsipas | 7-6,6-3 | |
| ATP Rome MD | 05/11 12:20 | 25 | Tsitsipas/Tsitsipas v Kubot/Skugor | 6-7,3-6 | |
| ATP Madrid MD | 05/04 14:55 | 25 | Koolhof/Kubot v Tsitsipas/Tsitsipas | 6-4,5-7,10-6 | |
| ATP Monte Carlo MD | 04/14 12:10 | 26 | Tsitsipas/Tsitsipas v Garin/Pella | 4-6,4-6 | |
| ATP Monte Carlo MD | 04/13 15:00 | 25 | Krawietz/Tecau v Tsitsipas/Tsitsipas | 6-7,6-3,9-11 | |
| ATP Marseille MD | 03/10 15:30 | 26 | Tsitsipas/Tsitsipas v Glasspool/Heliovaara | 5-7,1-6 |