Stadium: Centre Court Round: 27 Ground: Hardcourt indoor
| ATP Antwerp MD | 2023/10/17 10:30 | Reyes-Varela/Vega Hernandez v Tsitsipas/Tsitsipas | 6-7,6-7 |
| Davis Cup | 2023/09/17 08:00 | Tsitsipas/Tsitsipas v Klein/Zelenay | 3-6,7-6,3-6 |
| US Open MD | 2023/09/02 16:00 | Tsitsipas/Tsitsipas v Dodig/Krajicek | 5-7,7-6,4-6 |
| US Open MD | 2023/08/31 15:00 | Tsitsipas/Tsitsipas v Reyes-Varela/Vega Hernandez | 7-6,6-4 |
| Wimbledon MD | 2023/07/07 18:30 | Tsitsipas/Tsitsipas v Fils/Van Assche | 7-6,4-6,2-6 |
| The Boodles | 2023/07/01 15:00 | Tsitsipas/Tsitsipas v Cash/Johnson | 6-7,6-4,1-0 |
| French Open MD | 2023/05/30 12:40 | Tsitsipas/Tsitsipas v Arevalo/Rojer | 3-6,6-3,6-7 |
| ATP Madrid MD | 2023/04/28 17:20 | Tsitsipas/Tsitsipas v Arevalo/Rojer | 6-7,5-7 |
| ATP Antwerp MD | 2023/10/17 14:50 | Bergs/Colson v Middelkoop/Mies | 4-6,7-6,6-10 |
| ATP Shanghai MD | 2023/10/07 05:45 | Middelkoop/Mies v Bopanna/Ebden | 4-6,3-6 |
| French Open MD | 2023/06/08 11:25 | Middelkoop/Mies v Gille/Vliegen | 4-6,5-7 |
| French Open MD | 2023/06/05 16:25 | Middelkoop/Mies v Arevalo/Rojer | 7-6,6-1 |
| French Open MD | 2023/06/04 11:30 | Glasspool/Heliovaara v Middelkoop/Mies | 4-6,2-6 |
| French Open MD | 2023/06/02 11:35 | Eysseric/Mayot v Middelkoop/Mies | 5-7,3-6 |
| French Open MD | 2023/06/01 13:10 | Bublik/Fucsovics v Middelkoop/Mies | 3-6,1-6 |
| ATP Rome MD | 2023/05/14 16:20 | Koolhof/Skupski v Middelkoop/Mies | 6-7,6-3,10-4 |