| ITF - W75 Charlottesville | 04/28 17:00 | 29 | [84] Kayla Day v Louisa Chirico [283] | 1-6,5-7 | |
| ITF - W75 Charlottesville | 04/27 17:50 | 28 | [283] Louisa Chirico v Maya Joint [269] | 7-6,6-1 | |
| ITF - W75 Charlottesville | 04/26 15:00 | 27 | [283] Louisa Chirico v Valentini Grammatikopoulou [211] | 4-6,6-3,6-3 | |
| ITF - W75 Charlottesville | 04/25 13:50 | 26 | Allie Kiick v Louisa Chirico | Retired | |
| ITF - W75 Charlottesville | 04/23 19:00 | 25 | Ashton Bowers v Louisa Chirico | 3-6,4-6 | |
| ITF - W35 Boca Raton | 04/09 19:55 | 25 | Louisa Chirico v Ashton Bowers | 3-6,6-7 | |
| ITF - W75 Split | 04/02 16:45 | 25 | [158] Simona Waltert v Louisa Chirico [265] | 6-4,4-6,7-6 | |
| ITF - W35 Terrassa | 03/27 11:20 | 26 | [263] Louisa Chirico v Caijsa W Hennemann [467] | 3-6,4-6 | |
| ITF - W35 Terrassa | 03/25 14:25 | 25 | [263] Louisa Chirico v Maria Bondarenko [356] | 6-4,6-0 | |
| WTA - Charleston | 03/11 15:40 | 25 | [95] Kamilla Rakhimova v Louisa Chirico [257] | 6-4,6-4 | |
| WTA - Austin | 02/24 16:00 | 14 | [129] Jessika Ponchet v Louisa Chirico [243] | 7-5,6-3 | |
| ITF - W35 Wesley Chapel | 02/07 15:50 | 25 | [243] Louisa Chirico v Maribella Zamarripa [299] | 7-6,6-7,1-6 | |
| ITF - W75 Rome, GA | 02/01 17:40 | 26 | [248] Louisa Chirico v Robin Montgomery [198] | 2-6,1-6 | |
| ITF - W75 Rome, GA | 01/31 14:50 | 25 | [248] Louisa Chirico v Ava Markham [314] | 6-3,6-2 | |
| ITF - W75 Vero Beach | 01/24 18:10 | 25 | [258] Louisa Chirico v Yulia Starodubtseva [150] | 3-6,2-6 | |
| ITF - W35 Naples | 01/19 18:50 | 27 | [194] Robin Montgomery v Louisa Chirico [258] | 3-6,7-6,6-4 | |
| ITF - W35 Naples | 01/18 14:55 | 26 | [196] Maria Kozyreva v Louisa Chirico [258] | 5-7,6-7 | |
| ITF - W35 Naples | 01/17 20:10 | 25 | Sophia C-Ignatiev v Louisa Chirico | 1-6,2-6 | |
| ITF - W35 Naples | 01/13 15:00 | 28 | [261] Louisa Chirico v Clervie Ngounoue [492] | 2-6,5-7 | |
| ITF - W35 Naples | 01/12 15:55 | 27 | [261] Louisa Chirico v Ekaterine Gorgodze [333] | 7-6,3-6,6-3 | |
| ITF - W35 Naples | 01/11 18:30 | 26 | Louisa Chirico v Jessica Pieri | 6-7,6-1,6-3 | |
| ITF - W35 Naples | 01/10 14:50 | 25 | Louisa Chirico v Mayuka Aikawa | 7-5,6-3 | |
| ITF - W100 Charleston | 11/08 19:45 | 25 | [318] Varvara Lepchenko v Louisa Chirico [248] | Retired | |
| WTA - Midland | 10/30 16:15 | 19 | [223] Lulu Sun v Louisa Chirico [255] | 6-1,6-1 | |
| WTA - Midland | 10/29 19:35 | 14 | [353] Whitney Osuigwe v Louisa Chirico [255] | 6-7,6-2,3-6 | |
| ITF - W60 Toronto | 10/27 13:55 | 27 | [198] Jana Fett v Louisa Chirico [255] | 7-6,6-4 | |
| ITF - W60 Toronto | 10/26 18:30 | 26 | [466] Layne Sleeth v Louisa Chirico [255] | 2-6,4-6 | |
| ITF - W60 Toronto | 10/24 16:25 | 25 | [337] Robin Anderson v Louisa Chirico [255] | 6-7,4-6 | |
| ITF - W80 Macon | 10/17 20:20 | 25 | [134] Hailey Baptiste v Louisa Chirico [256] | 6-0,6-2 | |
| ITF - W60 Rancho Santa Fe | 10/13 19:45 | 27 | [218] Louisa Chirico v Yulia Starodubtseva [202] | 6-4,3-6,4-6 |