| ATP Shanghai MD | 10/06 07:35 | 25 | Glasspool/Heliovaara v Escobar/Nedovyesov | 4-6,4-6 | |
| ATP Astana MD | 09/29 10:45 | 26 | Behar/Pavlasek v Glasspool/Heliovaara | 7-6,4-6,10-7 | |
| Challenger Saint-Tropez MD | 09/23 09:30 | 28 | Glasspool/Heliovaara v Eysseric/Mayot | 6-7,4-6 | |
| Challenger Saint-Tropez MD | 09/22 11:35 | 27 | Glasspool/Heliovaara v Gornes/Verbeek | 7-6,7-6 | |
| Challenger Saint-Tropez MD | 09/21 09:30 | 26 | Glasspool/Heliovaara v Nedunchezhiyan/Raja | 6-2,6-2 | |
| US Open MD | 09/02 17:00 | 25 | Galloway/Olivetti v Glasspool/Heliovaara | 7-6,7-6 | |
| US Open MD | 08/30 17:20 | 24 | Melo/Peers v Glasspool/Heliovaara | 4-6,6-7 | |
| ATP Cincinnati MD | 08/16 19:30 | 25 | Glasspool/Heliovaara v Purcell/Rublev | 6-7,5-7 | |
| ATP Toronto MD | 08/08 15:00 | 25 | Hurkacz/Pavic v Glasspool/Heliovaara | 6-2,7-5 | |
| ATP Washington MD | 08/04 16:00 | 28 | McDonald/Shelton v Glasspool/Heliovaara | 3-6,6-3,12-10 | |
| ATP Washington MD | 08/02 20:00 | 27 | Glasspool/Heliovaara v Hurkacz/Tiafoe | 6-3,7-6 | |
| ATP Washington MD | 08/01 23:15 | 26 | Glasspool/Heliovaara v Martin/Nys | 3-6,6-2,12-10 | |
| ATP Hamburg MD | 07/25 15:45 | 26 | Glasspool/Heliovaara v Dellien/Pella | 3-6,3-6 | |
| French Open MD | 06/04 11:30 | 26 | Glasspool/Heliovaara v Middelkoop/Mies | 4-6,2-6 | |
| French Open MD | 06/01 11:45 | 25 | Glasspool/Heliovaara v Ivashka/Popyrin | 7-6,7-5 | |
| French Open MD | 05/30 15:10 | 24 | Glasspool/Heliovaara v Erler/Miedler | 7-6,4-6,6-3 | |
| Challenger Bordeaux MD | 05/20 11:15 | 29 | Glasspool/Heliovaara v Doumbia/Reboul | 6-4,6-2 | |
| Challenger Bordeaux MD | 05/19 10:15 | 28 | Glasspool/Heliovaara v Herbert/Mahut | 7-5,6-3 | |
| Challenger Bordeaux MD | 05/18 09:00 | 27 | Glasspool/Heliovaara v Chardy/Olivetti | 7-5,6-4 | |
| Challenger Bordeaux MD | 05/17 10:55 | 26 | Glasspool/Heliovaara v Frantzen/Jebens | 6-3,5-7,10-2 | |
| ATP Rome MD | 05/14 18:00 | 26 | Glasspool/Heliovaara v McDonald/Tiafoe | 6-4,2-6,9-11 | |
| ATP Rome MD | 05/13 15:45 | 25 | Glasspool/Heliovaara v Lammons/Peers | 7-6,2-6,10-6 | |
| ATP Madrid MD | 04/30 14:05 | 26 | Glasspool/Heliovaara v Auger Aliassime/Shapovalov | 4-6,2-6 | |
| ATP Madrid MD | 04/27 15:10 | 25 | Glasspool/Heliovaara v Hurkacz/Shelton | 6-4,7-6 | |
| ATP Barcelona MD | 04/22 12:30 | 28 | Gonzalez/Molteni v Glasspool/Heliovaara | 7-5,4-6,10-7 | |
| ATP Barcelona MD | 04/20 13:40 | 27 | Glasspool/Heliovaara v Ram/Salisbury | 7-6,7-5 | |
| ATP Barcelona MD | 04/17 12:00 | 26 | Glasspool/Heliovaara v Nys/Zielinski | 2-6,7-6,10-0 | |
| ATP Monte Carlo MD | 04/14 10:35 | 27 | Glasspool/Heliovaara v Arneodo/Weissborn | 2-6,6-7 | |
| ATP Monte Carlo MD | 04/13 09:00 | 26 | Glasspool/Heliovaara v Gonzalez/Molteni | 5-7,6-4,10-8 | |
| ATP Monte Carlo MD | 04/11 10:45 | 25 | Glasspool/Heliovaara v Mahut/Wawrinka | 6-3,6-4 |