| ATP Stockholm MD | 10/22 17:35 | 28 | Glasspool/Heliovaara v Cressy/Olivetti | 7-5,6-3 | |
| ATP Stockholm MD | 10/20 11:00 | 27 | Jebavy R / Pavlasek A v Glasspool/Heliovaara | 3-6,4-6 | |
| ATP Stockholm MD | 10/17 12:15 | 26 | Borg/Freund v Glasspool/Heliovaara | 3-6,2-6 | |
| ATP Nur-Sultan MD | 10/04 08:40 | 26 | Glasspool/Heliovaara v Hurkacz/Zielinski | 6-7,3-6 | |
| ATP Metz MD | 09/25 11:00 | 29 | Nys/Zielinski v Glasspool/Heliovaara | 7-6,6-4 | |
| ATP Metz MD | 09/24 14:35 | 28 | Mahut/Roger-Vasselin v Glasspool/Heliovaara | Retired | |
| ATP Metz MD | 09/22 10:00 | 27 | Added D / Olivetti A v Glasspool/Heliovaara | 6-7,4-6 | |
| ATP Metz MD | 09/20 16:55 | 26 | Gille/Vliegen v Glasspool/Heliovaara | 5-7,4-6 | |
| US Open MD | 09/07 00:15 | 27 | Cabal / Farah v Glasspool/Heliovaara | 7-6,6-2 | |
| US Open MD | 09/05 20:35 | 26 | Glasspool/Heliovaara v Kokkinakis T / Kyrgios N | 3-6,7-6,7-6 | |
| US Open MD | 09/02 16:00 | 25 | Glasspool/Heliovaara v Klaasen R / Melo M | 6-4,7-6 | |
| US Open MD | 08/31 17:40 | 24 | Glasspool/Heliovaara v Blumberg/Kecmanovic | 6-3,6-3 | |
| ATP Winston-Salem MD | 08/25 19:00 | 28 | Nys/Zielinski v Glasspool/Heliovaara | 6-4,7-6 | |
| ATP Winston-Salem MD | 08/24 20:00 | 27 | Glasspool/Heliovaara v Cabral/Skugor | 6-4,6-3 | |
| ATP Winston-Salem MD | 08/23 22:35 | 26 | Glasspool/Heliovaara v Mansouri/Thomson | 4-6,6-3,10-5 | |
| ATP Cincinnati MD | 08/18 21:10 | 26 | Puetz T / Venus M v Glasspool/Heliovaara | 4-6,7-6,10-8 | |
| ATP Cincinnati MD | 08/16 19:10 | 25 | Glasspool/Heliovaara v Paul T / Tiafoe F | 4-6,6-3,10-8 | |
| ATP Montreal MD | 08/12 18:35 | 27 | Koolhof/Skupski v Glasspool/Heliovaara | 4-6,6-3,10-8 | |
| ATP Montreal MD | 08/11 21:20 | 26 | Bolelli S / Fognini F v Glasspool/Heliovaara | 3-6,4-6 | |
| ATP Montreal MD | 08/10 15:00 | 25 | Glasspool/Heliovaara v Dodig/Krajicek | 6-4,6-2 | |
| ATP Umag MD | 07/30 20:30 | 29 | Bolelli S / Fognini F v Glasspool/Heliovaara | 5-7,7-6,10-7 | |
| ATP Umag MD | 07/29 14:00 | 28 | Glasspool/Heliovaara v Matos/Vega Hernandez | 6-1,5-7,10-8 | |
| ATP Umag MD | 07/28 16:00 | 27 | Poljicak/Serdarusic v Glasspool/Heliovaara | 3-6,3-6 | |
| ATP Umag MD | 07/26 16:40 | 26 | Arends S / Pel D v Glasspool/Heliovaara | 3-6,6-7 | |
| ATP Hamburg MD | 07/24 10:30 | 29 | Bopanna/Middelkoop v Glasspool/Heliovaara | 2-6,4-6 | |
| ATP Hamburg MD | 07/23 10:00 | 28 | Puetz T / Venus M v Glasspool/Heliovaara | 4-6,4-6 | |
| ATP Hamburg MD | 07/21 15:00 | 27 | Krawietz K / Mies A v Glasspool/Heliovaara | 1-6,6-7 | |
| ATP Hamburg MD | 07/18 11:15 | 26 | Glasspool/Heliovaara v Koolhof/Skupski | 7-5,6-2 | |
| Wimbledon MD | 07/03 10:00 | 26 | Glasspool/Heliovaara v Mektic/Pavic | 4-6,6-7,6-4,6-2,3-6 | |
| Wimbledon MD | 07/02 10:00 | 25 | Glasspool/Heliovaara v Blumberg/Ruud | 6-1,3-6,6-3,3-6,6-4 |