Stadium: Court 4 Round: 25 Ground: Clay
| ATP Madrid MD | 2019/05/10 21:15 | Rojer/Tecau v Koolhof/Tsitsipas | 6-4,5-7,10-5 |
| ATP Madrid MD | 2019/05/09 19:10 | Murray/Soares v Koolhof/Tsitsipas | 2-6,6-7 |
| ATP Madrid MD | 2019/05/08 17:40 | Koolhof/Tsitsipas v Mektic/Skugor | 6-2,6-4 |
| ATP Madrid MD | 2019/05/07 16:20 | Koolhof/Tsitsipas v Cecchinato/Fucsovics | 6-3,6-3 |
| ATP Miami MD | 2019/03/30 19:05 | Bryan/Bryan v Koolhof/Tsitsipas | 7-5,7-6 |
| ATP Miami MD | 2019/03/29 17:00 | Dodig/Roger-Vasselin v Koolhof/Tsitsipas | 3-6,7-6,8-10 |
| ATP Miami MD | 2019/03/28 00:00 | Isner/Querrey v Koolhof/Tsitsipas | 4-6,7-5,8-10 |
| ATP Miami MD | 2019/03/24 20:00 | Koolhof/Tsitsipas v Murray/Soares | 6-3,4-6,10-7 |