| ITF Women Stillwater | 09/28 15:00 | 26 | [473] Whoriskey, Caitlin v Wozniak, Aleksandra [335] | 3-6,1-6 | |
| ITF Women Stillwater | 09/26 19:40 | 25 | Katarina Stresnakova v Whoriskey, Caitlin | 1-6,0-6 | |
| ITF Women Lubbock | 09/19 18:15 | 25 | Whoriskey, Caitlin v James, Akilah | 2-6,6-3,4-6 | |
| ITF Women Redding | 09/15 19:30 | 27 | [135] Whoriskey, Caitlin v Jovic, J. [337] | 7-5,2-6,5-7 | |
| ITF Women Redding | 09/14 19:45 | 26 | Guillermo, Lorraine M v Whoriskey, Caitlin | 2-6,6-7 | |
| ITF Women Redding | 09/13 20:50 | 25 | Facey, Kat v Whoriskey, Caitlin | 0-6,3-6 | |
| ITF Women Landisville | 08/09 18:00 | 25 | Whoriskey, Caitlin v Stewart, Katerina | 6-3,6-7,5-7 | |
| ITF Women Landisville Qual | 08/08 15:30 | 62 | [369] Whoriskey, Caitlin v Yurovsky, Ronit [387] | 6-2,3-6,7-5 | |
| ITF Women Landisville Qual | 08/07 14:00 | 62 | Whoriskey, Caitlin v James, Akilah | 6-2,6-3 | |
| ITF Women Landisville Qual | 08/06 17:00 | 62 | Whoriskey, Caitlin v Dunleavy, Caroline | 6-1,6-2 | |
| ITF Women Fort Worth | 08/01 17:10 | 25 | [373] Whoriskey, Caitlin v Guarachi Mathison, Alexa [421] | 5-7,2-6 | |
| ITF Women Evansville | 07/28 15:35 | 27 | Whoriskey, Caitlin v Guillermo, Lorraine M | 3-6,0-6 | |
| ITF Women Evansville | 07/27 18:00 | 26 | Whoriskey, Caitlin v Douglas, Ellie | 6-3,3-6,6-3 | |
| ITF Women Evansville | 07/25 16:00 | 25 | Whoriskey, Caitlin v Bondarenko, Alona | 7-5,6-1 | |
| ITF Women Ilkley Qual | 06/18 10:00 | 54 | [177] Destanee Aiava v Whoriskey, Caitlin [298] | 6-3,2-6,6-4 | |
| WTA Nottingham Qual | 06/10 13:25 | 45 | [180] Lizette Cabrera v Whoriskey, Caitlin [305] | 6-2,6-1 | |
| ITF Women Surbiton Qual | 06/03 14:00 | 54 | [370] Katie Swan v Whoriskey, Caitlin [305] | 7-6,7-6 | |
| ITF Women Surbiton Qual | 06/03 10:00 | 54 | [135] Lister, Cornelia v Whoriskey, Caitlin [305] | 6-1,2-6,2-6 | |
| ITF Women Naples | 05/18 14:50 | 26 | [464] Sophie Chang v Whoriskey, Caitlin [307] | 6-2,6-2 | |
| ITF Women Naples | 05/17 17:30 | 25 | [393] Zlochova, Zuzana v Whoriskey, Caitlin [307] | 3-6,3-6 | |
| ITF Women Charleston | 05/02 15:20 | 25 | Whoriskey, Caitlin v Claire Liu | 3-6,2-6 | |
| ITF Women Charlottesville | 04/26 20:30 | 25 | [279] Victoria Rodriguez v Whoriskey, Caitlin [305] | 6-3,6-2 | |
| ITF Women Dothan | 04/18 18:50 | 25 | [304] Whoriskey, Caitlin v Pella, Catalina [330] | 2-6,4-6 | |
| WTA Monterrey Qual | 04/02 18:00 | 46 | [319] Whoriskey, Caitlin v Beatriz Haddad Maia [166] | 3-6,6-2,3-6 | |
| WTA Monterrey Qual | 04/01 18:05 | 45 | [280] Jovic, J. v Whoriskey, Caitlin [319] | 3-6,5-7 | |
| ITF Women Midland Qual | 01/29 16:20 | 54 | Whoriskey, Caitlin v Katherine Sebov | 5-7,3-6 | |
| ITF Women Waco | 11/09 20:30 | 25 | Whoriskey, Caitlin v Elie, Jennifer | 2-6,5-7 | |
| ITF Women Waco Qual | 11/08 16:00 | 54 | Whoriskey, Caitlin v Melichar, Nicole | 2-6,6-1,6-4 | |
| ITF Women Waco Qual | 11/07 18:00 | 54 | Whoriskey, Caitlin v Jessica Hinojosa Gomez | 6-2,6-3 | |
| ITF Women Toronto | 11/01 17:50 | 25 | Whoriskey, Caitlin v Elise Mertens | 0-6,4-6 |