| ATP Miami MD | 03/29 19:05 | 27 | Lammons/Withrow v Glasspool/Heliovaara | 7-6,3-6,11-9 | |
| ATP Miami MD | 03/27 17:15 | 26 | Bublik/Kecmanovic v Glasspool/Heliovaara | 2-6,2-6 | |
| ATP Miami MD | 03/25 20:05 | 25 | Cressy/Mies v Glasspool/Heliovaara | 3-6,1-6 | |
| ATP Indian Wells MD | 03/17 01:00 | 27 | Gonzalez/Roger-Vasselin v Glasspool/Heliovara | 2-6,6-2,10-7 | |
| ATP Indian Wells MD | 03/14 03:00 | 26 | Giron/Wolf v Glasspool/Heliovara | 2-6,3-6 | |
| ATP Indian Wells MD | 03/12 01:00 | 25 | Middelkoop/Van De Zandschulp v Glasspool/Heliovara | 3-6,6-3,6-10 | |
| ATP Dubai MD | 03/04 12:30 | 29 | Glasspool/Heliovaara v Cressy/Martin | 6-7,4-6 | |
| ATP Dubai MD | 03/03 11:00 | 28 | Mektic/Pavic v Glasspool/Heliovaara | 4-6,2-6 | |
| ATP Dubai MD | 03/02 11:00 | 27 | Glasspool/Heliovaara v Bhambri/Myneni | 6-2,6-2 | |
| ATP Dubai MD | 02/28 14:25 | 26 | Glasspool/Heliovaara v Krawietz/Puetz | 7-6,6-2 | |
| ATP Rotterdam MD | 02/17 10:00 | 27 | Glasspool/Heliovaara v Bopanna/Ebden | 2-6,1-6 | |
| ATP Rotterdam MD | 02/13 10:00 | 26 | Glasspool/Heliovaara v Tsitsipas/Tsitsipas | 6-3,6-4 | |
| Australian Open MD | 01/21 11:50 | 25 | Hijikata/Kubler v Glasspool/Heliovaara | 3-6,7-5,6-2 | |
| Australian Open MD | 01/20 00:00 | 24 | Lammons/Withrow v Glasspool/Heliovaara | 6-7,3-6 | |
| ATP Adelaide 2 MD | 01/13 02:50 | 28 | Glasspool/Heliovaara v Arevalo/Rojer | Walkover | |
| ATP Adelaide 2 MD | 01/12 07:35 | 27 | Mahut/Puetz v Glasspool/Heliovaara | 6-7,6-3,5-10 | |
| ATP Adelaide 2 MD | 01/11 10:35 | 26 | McDonald/Melo v Glasspool/Heliovaara | 6-7,3-6 | |
| ATP Adelaide MD | 01/08 03:30 | 29 | Glasspool/Heliovaara v Murray/Venus | 6-3,7-6 | |
| ATP Adelaide MD | 01/07 01:30 | 28 | McDonald/Melo v Glasspool/Heliovaara | 2-6,3-6 | |
| ATP Adelaide MD | 01/06 00:30 | 27 | Glasspool/Heliovaara v Haase/Middelkoop | 6-3,5-7,10-6 | |
| ATP Adelaide MD | 01/04 02:30 | 26 | Glasspool/Heliovaara v Erler/Miedler | 6-3,7-6 | |
| ATP World Tour Finals MD | 11/19 17:30 | 28 | Mektic/Pavic v Glasspool/Heliovaara | 6-4,6-7,10-6 | |
| ATP World Tour Finals MD | 11/17 10:30 | 3 | Glasspool/Heliovaara v Granollers/Zeballos | 6-0,6-4 | |
| ATP World Tour Finals MD | 11/15 17:30 | 2 | Ram/Salisbury v Glasspool/Heliovaara | 7-5,6-4 | |
| ATP World Tour Finals MD | 11/13 10:30 | 1 | Arevalo/Rojer v Glasspool/Heliovaara | 5-7,6-7 | |
| ATP Paris MD | 11/05 10:30 | 28 | Glasspool/Heliovaara v Koolhof/Skupski | 1-6,7-6,6-10 | |
| ATP Paris MD | 11/04 14:30 | 27 | Glasspool/Heliovaara v Ebden/Murray | 6-3,7-6 | |
| ATP Paris MD | 11/03 13:15 | 26 | Glasspool/Heliovaara v Evans/Peers | 6-3,6-7,15-13 | |
| ATP Basel MD | 10/26 12:30 | 26 | Glasspool/Heliovaara v Golubev/Nedovyesov | 5-7,6-4,3-10 | |
| ATP Stockholm MD | 10/23 11:00 | 29 | Arevalo/Rojer v Glasspool/Heliovaara | 6-3,6-3 |