| WTA Doha | 02/18 08:00 | 14 | [125] Maddison Inglis v Kristina Kucova [77] | 0-6,2-6 | |
| WTA Dubai | 02/13 11:35 | 19 | [129] Maddison Inglis v Katerina Siniakova [44] | Retired | |
| WTA Dubai | 02/12 11:50 | 14 | [129] Maddison Inglis v Sara Errani [145] | 7-6,7-6 | |
| Open de Australia - Femenino | 01/22 03:00 | 25 | [115] Kaia Kanepi v Maddison Inglis [133] | 2-6,6-2,6-0 | |
| Open de Australia - Femenino | 01/20 01:40 | 24 | [165] Hailey Baptiste v Maddison Inglis [133] | 6-7,6-2,2-6 | |
| Open de Australia - Femenino | 01/18 02:45 | 23 | [133] Maddison Inglis v Leylah Fernandez [24] | 6-4,6-2 | |
| WTA Adelaide 2 | 01/12 10:45 | 26 | [31] Tamara Zidansek v Maddison Inglis [139] | 6-2,6-1 | |
| WTA Adelaide 2 | 01/11 00:30 | 25 | [139] Maddison Inglis v Danka Kovinic [99] | 6-4,1-6,6-2 | |
| WTA Adelaida | 01/04 00:30 | 25 | [141] Maddison Inglis v Shelby Rogers [40] | 1-6,3-6 | |
| WTA Adelaida | 01/03 02:55 | 19 | [141] Maddison Inglis v Irene Burillo Escorihuela [215] | 6-1,6-4 | |
| WTA Adelaida | 01/02 02:20 | 14 | [141] Maddison Inglis v Alexandra Bozovic [451] | 6-4,6-4 | |
| WTA Midland | 11/01 20:20 | 25 | [415] Katrina Scott v Maddison Inglis [139] | 6-4,6-4 | |
| ITF W25 Austin | 10/27 23:25 | 25 | Maddison Inglis v Charlotte Chavatipon | Cancelled | |
| ITF W80 Macon | 10/20 14:00 | 25 | [370] Louisa Chirico v Maddison Inglis [127] | 6-3,6-2 | |
| ITF W60 Rancho Santa Fe | 10/13 18:45 | 25 | [157] Rebecca Marino v Maddison Inglis [127] | 6-4,6-3 | |
| WTA Indian Wells | 10/05 19:35 | 19 | [127] Maddison Inglis v Alycia Parks [245] | 3-6,4-6 | |
| WTA Indian Wells | 10/04 19:15 | 14 | [127] Maddison Inglis v Mariam Bolkvadze [184] | 7-6,6-2 | |
| WTA Chicago | 09/29 14:00 | 25 | [12] Belinda Bencic v Maddison Inglis [130] | 5-7,6-1,6-0 | |
| WTA Chicago | 09/27 16:45 | 24 | [130] Maddison Inglis v Caroline Dolehide [181] | 4-6,6-2,6-4 | |
| WTA Chicago | 09/26 15:00 | - | [131] Maddison Inglis v Asia Muhammad [184] | 6-7,6-4,7-6 | |
| WTA Chicago | 09/25 15:00 | 25 | [131] Maddison Inglis v Julia Lohoff [71] | 6-2,6-2 | |
| WTA Columbus | 09/22 00:30 | 25 | [131] Maddison Inglis v Louisa Chirico [432] | 3-6,6-1,2-6 | |
| ITF W60 Caldas da Rainha | 09/18 15:00 | 28 | [94] Saisai Zheng v Maddison Inglis [139] | 6-2,6-3 | |
| ITF W60 Caldas da Rainha | 09/17 15:15 | 27 | [139] Maddison Inglis v Anastasia Kulikova [360] | 6-2,4-6,6-3 | |
| ITF W60 Caldas da Rainha | 09/16 09:00 | 26 | [139] Maddison Inglis v Natalija Stevanovic [248] | 6-2,6-1 | |
| ITF W60 Caldas da Rainha | 09/14 12:05 | 25 | [139] Maddison Inglis v Weronika Falkowska [408] | 3-6,7-5,6-3 | |
| WTA Karlsruhe | 09/08 11:50 | 25 | [144] Maddison Inglis v Katarzyna Kawa [164] | Retired | |
| US Open - Femenino | 08/24 21:40 | 14 | [216] Monica Niculescu v Maddison Inglis [144] | 6-4,6-7,6-2 | |
| WTA Montreal | 08/07 16:30 | 14 | [84] Amanda Anisimova v Maddison Inglis [146] | 6-3,1-6,6-0 | |
| WTA Concord | 08/02 19:20 | 25 | [146] Maddison Inglis v Madison Brengle [78] | Retired |