| Wimbledon MD | 06/29 16:55 | 24 | Glasspool/Heliovaara v Gaston/Musetti | 6-3,6-3,6-4 | |
| ATP Eastbourne MD | 06/22 13:15 | 27 | Murray/Soares v Glasspool/Heliovaara | 6-4,7-5 | |
| ATP Eastbourne MD | 06/21 14:15 | 26 | Goransson/Mclachlan v Glasspool/Heliovaara | 6-7,7-6,4-10 | |
| ATP Queens MD | 06/19 14:50 | 29 | Glasspool/Heliovara v Mektic/Pavic | 6-3,6-7,6-10 | |
| ATP Queens MD | 06/18 16:30 | 28 | Glasspool/Heliovara v Bopanna/Shapovalov | 7-5,6-7,10-4 | |
| ATP Queens MD | 06/16 15:20 | 27 | Ram/Salisbury v Glasspool/Heliovara | 6-7,2-6 | |
| ATP Queens MD | 06/14 18:10 | 26 | Mahut/Roger-Vasselin v Glasspool/Heliovara | 5-7,3-6 | |
| French Open MD | 05/30 16:45 | 27 | Glasspool/Heliovaara v Bopanna/Middelkoop | 6-4,4-6,6-7 | |
| French Open MD | 05/28 10:30 | 26 | Nys/Zielinski v Glasspool/Heliovaara | 6-7,3-6 | |
| French Open MD | 05/27 10:55 | 25 | Behar/Escobar v Glasspool/Heliovaara | 4-6,2-6 | |
| French Open MD | 05/25 15:00 | 24 | Glasspool/Heliovaara v Krawietz/Mies | 6-4,6-2 | |
| ATP Geneva MD | 05/16 14:00 | 26 | Andujar/Middelkoop v Glasspool/Heliovaara | Cancelled | |
| ATP Rome MD | 05/13 12:40 | 27 | Glasspool/Heliovaara v Isner/Schwartzman | 3-6,2-6 | |
| ATP Rome MD | 05/12 12:05 | 26 | Glasspool/Heliovaara v Kokkinakis/Tiafoe | 6-3,3-6,10-8 | |
| ATP Rome MD | 05/11 13:50 | 25 | Ram/Salisbury v Glasspool/Heliovaara | 6-7,3-6 | |
| Challenger Aix en Provence MD | 05/05 08:30 | 27 | Wayenburg/Van Assche v Glasspool/Heliovaara | 6-4,3-6,11-9 | |
| Challenger Aix en Provence MD | 05/04 10:45 | 26 | Arneodo/Walkow v Glasspool/Heliovaara | 4-6,7-6,4-10 | |
| ATP Munich MD | 04/30 09:30 | 28 | Krawietz/Mies v Glasspool/Heliovaara | 7-5,6-3 | |
| ATP Munich MD | 04/28 12:15 | 27 | Glasspool/Heliovaara v Peers/Polasek | 7-6,7-6 | |
| ATP Munich MD | 04/27 14:05 | 26 | Cornea/Tsitsipas v Glasspool/Heliovaara | 4-6,1-6 | |
| ATP Belgrade MD | 04/18 15:00 | 26 | Glasspool/Heliovaara v Behar/Escobar | 4-6,3-6 | |
| ATP Marrakech MD | 04/06 17:00 | 26 | Cecchinato/Musetti v Glasspool/Heliovaara | 6-4,1-6,10-7 | |
| ATP Marrakech MD | 04/06 14:25 | 26 | Evans/Skupski v Glasspool/Heliovaara | Cancelled | |
| ATP Acapulco MD | 02/26 04:00 | 28 | Glasspool/Heliovaara v Lopez/Tsitsipas | 4-6,4-6 | |
| ATP Acapulco MD | 02/25 01:00 | 27 | Glasspool/Heliovaara v Murray/Soares | 4-6,6-3,10-6 | |
| ATP Acapulco MD | 02/23 03:35 | 26 | Melo/Zverev v Glasspool/Heliovaara | 2-6,6-4,6-10 | |
| ATP Acapulco MD | 02/21 03:05 | 19 | Saville/Smith v Glasspool/Heliovaara | 6-4,4-6,10-4 | |
| ATP Acapulco MD | 02/20 04:00 | 14 | Reyes-Varela/Schnur v Glasspool/Heliovaara | 3-6,4-6 | |
| ATP Delray Beach MD | 02/16 16:00 | 26 | Glasspool/Heliovaara v Krajicek/Nys | 6-7,5-7 | |
| ATP Dallas MD | 02/13 21:10 | 29 | Arevalo/Rojer v Glasspool/Heliovaara | 7-6,6-4 |