| WTA - Indian Wells | 03/04 20:15 | 25 | [179] Olga Danilovic v Maria Mateas [413] | 6-3,6-0 | |
| WTA - Indian Wells | 03/04 20:15 | 25 | Olga Danilovic v Patricia Maria Tig | Cancelled | |
| WTA - Indian Wells | 03/02 20:55 | 24 | [179] Olga Danilovic v Veronica Cepede Royg [151] | 1-6,6-4,6-4 | |
| ITF W25 Rancho Santa Fe | 02/27 19:00 | 27 | [249] Hailey Baptiste v Olga Danilovic [178] | 4-6,6-3,6-0 | |
| ITF W25 Rancho Santa Fe | 02/26 19:45 | 26 | [308] Ana Sofia Sanchez v Olga Danilovic [178] | 4-6,3-6 | |
| ITF W25 Rancho Santa Fe | 02/24 21:10 | 25 | [394] Lorraine M. Guillermo v Olga Danilovic [178] | 4-6,6-2,1-6 | |
| Fed Cup 2020 | 02/08 08:50 | - | [174] Olga Danilovic v Kaja Juvan [123] | 2-6,2-6 | |
| Fed Cup 2020 | 02/06 14:55 | 1 | Olga Danilovic v Laura Correia | 6-1,6-2 | |
| Australian Open - Feminin | 01/17 02:30 | 45 | [106] Varvara Gracheva v Olga Danilovic [185] | 6-2,4-6,6-1 | |
| Australian Open - Feminin | 01/16 03:10 | 44 | Olga Danilovic v Jovana Jovic | 3-6,6-3,7-6 | |
| WTA - Houston | 11/12 19:05 | 25 | [188] Olga Danilovic v Ann Li [147] | 1-6,5-7 | |
| WTA - Houston | 11/10 18:40 | 24 | [187] Olga Danilovic v Shelby Rogers [174] | 6-3,7-6 | |
| ITF - W25 Malibu | 11/07 17:20 | 26 | Olga Danilovic v Ashley Lahey | 6-7,6-2,3-6 | |
| ITF - W25 Malibu | 11/06 17:00 | 25 | [187] Olga Danilovic v Maegan Manasse [204] | Retired | |
| ITF - W25 Istanbul | 10/24 09:00 | 27 | [194] Olga Danilovic v Kamilla Rakhimova [243] | 1-6,6-1,5-7 | |
| ITF - W25 Istanbul | 10/23 11:10 | 26 | [194] Olga Danilovic v Jule Niemeier [299] | 7-6,6-1 | |
| ITF - W25 Istanbul | 10/22 09:35 | 25 | [194] Olga Danilovic v Lucia Bronzetti [352] | Retired | |
| WTA - Moscova | 10/13 10:15 | 46 | Isabella Shinikova v Olga Danilovic | 6-4,2-6,6-2 | |
| WTA - Moscova | 10/12 12:25 | 45 | [207] Olga Danilovic v Sofya Lansere [336] | 3-6,6-4,6-0 | |
| ITF W25 Kaposvar | 09/25 12:40 | 25 | Emiliana Arango v Olga Danilovic | 6-3,6-3 | |
| ITF - W60 Montreux | 09/08 12:00 | 29 | [266] Julia Grabher v Olga Danilovic [218] | 2-6,3-6 | |
| ITF - W60 Montreux | 09/07 13:20 | 28 | [218] Olga Danilovic v Alice Rame [500] | 6-0,6-3 | |
| ITF - W60 Montreux | 09/06 15:45 | 27 | [218] Olga Danilovic v Simona Waltert [323] | 6-2,4-6,6-1 | |
| ITF - W60 Montreux | 09/05 15:50 | 26 | [218] Olga Danilovic v Eleonora Molinaro [343] | 6-1,6-1 | |
| ITF - W60 Montreux | 09/04 11:20 | 25 | Olga Danilovic v Sara Cakarevic | 6-1,6-2 | |
| ITF - W25 Viena | 08/27 12:45 | 25 | [218] Olga Danilovic v Monika Kilnarova [485] | Retired | |
| ITF - W25 Leipzig | 08/17 11:00 | 28 | [244] Olga Danilovic v Jule Niemeier [325] | 2-6,6-7 | |
| ITF - W25 Leipzig | 08/16 15:00 | 27 | [252] Julia Grabher v Olga Danilovic [244] | 2-6,5-7 | |
| ITF - W25 Leipzig | 08/15 09:00 | 26 | [349] Sofya Lansere v Olga Danilovic [244] | 1-6,3-6 | |
| ITF - W25 Leipzig | 08/14 10:20 | 25 | Lisa Matviyenko v Olga Danilovic | 3-6,0-6 |