| ITF Women Toowoomba | 10/10 03:30 | 25 | Olivia Rogowska v Gergana Topalova | Retired | |
| ITF Women Brisbane | 10/05 01:40 | 27 | [165] Olivia Rogowska v Kimberly Birrell [259] | 4-6,3-6 | |
| ITF Women Brisbane | 10/04 03:00 | 26 | Olivia Rogowska v Gabriella Da Silva Fick | 7-5,6-4 | |
| ITF Women Brisbane | 10/03 02:45 | 25 | Olivia Rogowska v Abigail Tere-Apisah | 6-4,6-3 | |
| ITF Women Darwin | 09/28 01:00 | 27 | [157] Olivia Rogowska v Kimberly Birrell [307] | 6-7,3-6 | |
| ITF Women Darwin | 09/27 05:00 | 26 | [157] Olivia Rogowska v Georgia Brescia [314] | 6-3,6-2 | |
| ITF Women Darwin | 09/25 03:35 | 25 | [157] Olivia Rogowska v Olivia Tjandramulia [370] | 6-4,6-1 | |
| ITF Women Cairns | 09/20 03:05 | 26 | [162] Olivia Rogowska v Alison Bai [383] | 6-7,6-7 | |
| ITF Women Cairns | 09/19 04:40 | 25 | Olivia Rogowska v Marianna Zakarlyuk | 6-3,6-3 | |
| US Open Women | 08/22 16:35 | 44 | [159] Olivia Rogowska v Beatriz Haddad Maia [132] | 6-7,1-6 | |
| ITF Women Landisville | 08/09 17:30 | 26 | [173] Priscilla Hon v Olivia Rogowska [160] | 6-2,7-5 | |
| ITF Women Landisville | 08/07 16:50 | 25 | [160] Olivia Rogowska v Lauren Davis [201] | 7-6,6-4 | |
| WTA Washington | 08/01 23:20 | 25 | [62] Magda Linette v Olivia Rogowska [159] | 6-4,6-1 | |
| ITF Women Ashland | 07/25 18:25 | 25 | Olivia Rogowska v Gail Brodsky | 3-6,6-4,5-7 | |
| ITF Women Gatineau | 07/18 14:00 | 26 | Alicia Barnett v Olivia Rogowska | 6-0,6-1 | |
| ITF Women Gatineau | 07/16 15:35 | 25 | [389] Olivia Tjandramulia v Olivia Rogowska [153] | 3-6,4-6 | |
| ITF Women Surbiton | 06/04 11:00 | 25 | [153] Olivia Rogowska v Danielle Lao [249] | 4-6,4-6 | |
| French Open Women Qual | 05/22 12:20 | 44 | [154] Olivia Rogowska v Kathinka Von Deichmann [190] | 7-5,6-7,3-6 | |
| ITF Women Saint Gaudens | 05/14 11:30 | 25 | [224] Jaimee Fourlis v Olivia Rogowska [153] | 6-4,4-6,6-4 | |
| ITF Women Cagnes-Sur-Mer | 05/08 13:25 | 25 | [153] Olivia Rogowska v Dayana Yastremska [180] | 5-7,2-6 | |
| ITF Women Balatonboglar | 05/02 09:00 | 26 | Olivia Rogowska v Daniela Vismane | 4-6,2-6 | |
| ITF Women Balatonboglar | 05/01 08:00 | 25 | [148] Olivia Rogowska v Kimberley Zimmermann [324] | 6-3,6-2 | |
| ITF Women Kashiwa | 04/03 02:35 | 25 | [223] Destanee Aiava v Olivia Rogowska [148] | 6-3,6-2 | |
| ITF Women Kofu | 03/28 01:00 | 25 | [454] Julia Wachaczyk v Olivia Rogowska [145] | 4-6,6-3,6-3 | |
| WTA Miami Qual | 03/19 14:00 | 44 | [145] Olivia Rogowska v Yanina Wickmayer [109] | 4-6,7-6,4-6 | |
| WTA Acapulco Qual | 02/26 01:10 | - | Rebecca Peterson v Olivia Rogowska | 6-2,6-1 | |
| WTA Acapulco Qual | 02/25 03:20 | 45 | Arantxa P Santonja v Olivia Rogowska | 5-7,6-2,5-7 | |
| ITF Women Burnie | 02/02 01:00 | 28 | Viktorija Golubic v Olivia Rogowska | 6-7,6-0,6-2 | |
| ITF Women Burnie | 02/01 01:00 | 27 | Olivia Rogowska v Destanee Aiava | 6-2,6-3 | |
| ITF Women Burnie | 01/30 23:00 | 26 | Olivia Rogowska v Ellen Perez | 7-6,6-3 |