Stadium: Grandstand Round: 25 Ground: Clay
| ITF Women Charlottesville | 2018/04/26 13:30 | Allie Kiick v Louisa Chirico | 3-6,6-3,6-2 |
| ITF W100 Bonita Springs | 2019/05/07 15:30 | Louisa Chirico v Kayla Day | 6-4,7-5 |
| ITF W100 Bonita Springs | 2019/05/06 17:20 | Louisa Chirico v Martina Frantova | 6-0,6-2 |
| ITF W100 Charleston | 2019/05/03 17:20 | Louisa Chirico v Whitney Osuigwe | 0-6,4-6 |
| ITF W100 Charleston | 2019/05/02 19:00 | Deniz Khazaniuk v Louisa Chirico | 6-3,5-7,2-6 |
| ITF W100 Charleston | 2019/05/01 18:35 | Louisa Chirico v Caroline Dolehide | 6-0,6-4 |
| ITF W100 Charleston | 2019/04/30 14:00 | Louisa Chirico v Gabriela Talaba | 6-3,6-1 |
| ITF W100 Charleston | 2019/04/29 14:00 | Louisa Chirico v Rhiann Newborn | 6-7,6-0,10-3 |
| ITF W80 Charlottesville | 2019/04/25 15:40 | Anhelina Kalinina v Louisa Chirico | 6-3,6-3 |
| ITF W100 Charleston | 2019/05/01 14:00 | Allie Kiick v Emma Navarro | 3-6,0-6 |
| ITF W80 Dothan | 2019/04/18 15:00 | Lucie Hradecka v Allie Kiick | 6-3,6-4 |
| WTA Charleston | 2019/04/03 16:00 | Allie Kiick v Belinda Bencic | 0-6,3-6 |
| WTA Charleston | 2019/04/01 17:00 | Pauline Parmentier v Allie Kiick | 3-6,0-6 |
| WTA Miami | 2019/03/18 14:00 | Allie Kiick v Jessica Pegula | 5-7,0-6 |
| WTA Indian Wells | 2019/03/04 20:40 | Katie Boulter v Allie Kiick | 7-5,5-7,6-2 |
| WTA Indian Wells | 2019/02/26 22:55 | Kaia Kanepi v Allie Kiick | 6-0,6-2 |
| WTA Indian Wells | 2019/02/26 00:05 | Allie Kiick v Sara Errani | 6-3,5-7,6-2 |