| ITF W60 Playford | 10/28 00:30 | 27 | [195] Maddison Inglis v Olivia Gadecki [221] | 3-6,7-5,6-1 | |
| ITF W60 Playford | 10/27 01:30 | 26 | [195] Maddison Inglis v Naiktha Bains [347] | 6-4,6-4 | |
| ITF W60 Playford | 10/25 23:30 | 25 | Maddison Inglis v Lisa Mays | 6-0,3-6,6-3 | |
| WTA Seoul | 09/20 03:00 | 25 | [137] Maddison Inglis v Ankita Raina [329] | 6-4,5-7,1-6 | |
| ITF W60 Caldas da Rainha | 09/15 14:30 | 26 | [424] Adriana Reami v Maddison Inglis [129] | Retired | |
| ITF W60 Caldas da Rainha | 09/14 16:45 | 25 | [199] Matilde Jorge v Maddison Inglis [129] | 5-7,5-7 | |
| ITF W25 Santarém | 09/07 15:20 | 25 | [457] Maria Jose Portillo Ramirez v Maddison Inglis [134] | Retired | |
| US Open - Femenino | 08/26 15:00 | 19 | [142] Yue Yuan v Maddison Inglis [135] | 6-1,6-0 | |
| US Open - Femenino | 08/25 15:00 | 15 | Valerie Glozman v Maddison Inglis | 4-6,3-6 | |
| US Open - Femenino | 08/23 18:05 | 14 | [146] Ekaterine Gorgodze v Maddison Inglis [135] | 5-7,6-3,6-7 | |
| WTA Vancouver | 08/19 18:00 | 27 | [87] Rebecca Peterson v Maddison Inglis [140] | 6-1,7-6 | |
| WTA Vancouver | 08/18 17:00 | 26 | [140] Maddison Inglis v Xinyu Wang [82] | 6-3,6-2 | |
| WTA Vancouver | 08/15 21:50 | 25 | [140] Maddison Inglis v Harmony Tan [110] | 7-6,1-6,6-1 | |
| Wimbledon - Femenino | 06/27 16:50 | 23 | [129] Maddison Inglis v Dalma Galfi [89] | 7-5,3-6,4-6 | |
| Wimbledon - Femenino | 06/23 13:25 | 19 | [129] Maddison Inglis v Natalija Stevanovic [255] | 7-6,2-6,6-2 | |
| Wimbledon - Femenino | 06/22 16:15 | 15 | [129] Maddison Inglis v Mandy Minella [260] | 7-6,3-6,6-2 | |
| Wimbledon - Femenino | 06/21 12:50 | 14 | [129] Maddison Inglis v Indy De Vroome [258] | 7-6,6-1 | |
| WTA Birmingham | 06/12 13:00 | 19 | [127] Maddison Inglis v Catherine McNally [229] | 3-6,6-4,1-6 | |
| WTA Birmingham | 06/11 15:10 | 14 | [127] Maddison Inglis v Sarah Beth Grey [301] | 6-4,6-2 | |
| WTA Nottingham | 06/06 14:25 | 19 | [127] Maddison Inglis v Katie Boulter [136] | 6-3,2-6,3-6 | |
| WTA Nottingham | 06/04 13:15 | 14 | Maddison Inglis v Ella Mcdonald | 6-2,6-1 | |
| Open de Francia - Femenino | 05/16 09:50 | 14 | [169] Suzan Lamens v Maddison Inglis [126] | 6-2,6-2 | |
| WTA París | 05/10 15:25 | 25 | [127] Maddison Inglis v Diane Parry [96] | 1-6,4-6 | |
| WTA Saint-Malo | 05/03 09:00 | 25 | [65] Beatriz Haddad Maia v Maddison Inglis [126] | 6-2,6-0 | |
| WTA Madrid | 04/26 15:30 | 14 | [73] Varvara Gracheva v Maddison Inglis [126] | 6-2,6-3 | |
| WTA Stuttgart | 04/16 09:00 | 45 | [124] Maddison Inglis v Nastasja Schunk [222] | 6-4,4-6,1-6 | |
| WTA Miami | 03/21 19:10 | 14 | [126] Maddison Inglis v Ekaterine Gorgodze [123] | 7-6,4-6,5-7 | |
| WTA Indian Wells | 03/07 20:45 | 14 | [124] Maddison Inglis v Dalma Galfi [105] | 6-4,3-6,3-6 | |
| ITF W60 Arcadia | 03/03 19:40 | 26 | [322] Louisa Chirico v Maddison Inglis [129] | 6-3,7-5 | |
| ITF W60 Arcadia | 03/02 22:10 | 25 | [321] Elvina Kalieva v Maddison Inglis [129] | 1-6,1-6 |