Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| 2018 Fed Cup | 2018/02/11 15:35 | Deborah Chiesa v Lara Arruabarrena | 6-4,2-6,7-6 |
| WTA St. Petersburg Qual | 2018/01/29 10:35 | Deborah Chiesa v Elena Rybakina | 1-6,3-6 |
| WTA St. Petersburg Qual | 2018/01/28 12:45 | Deborah Chiesa v Jana Fett | 6-2,2-6,6-4 |
| WTA St. Petersburg Qual | 2018/01/27 19:15 | Kirsten Flipkens v Deborah Chiesa | 2-6,0-6 |
| ITF Women Andrezieux-Boutheon | 2018/01/22 12:55 | Deborah Chiesa v Sherazad Reix | 6-3,3-6,4-6 |
| Australian Open Women Qual | 2018/01/11 01:00 | Deborah Chiesa v Antonia Lottner | 6-2,6-7,3-6 |
| WTA Auckland Qual | 2017/12/31 23:05 | Deborah Chiesa v Sachia Vickery | 4-6,3-6 |
| WTA Auckland Qual | 2017/12/31 02:05 | Tereza Mrdeza v Deborah Chiesa | 1-6,4-6 |
| ITF Women Altenkirchen | 2018/02/21 16:25 | Lena Papadakis v Valentini Grammatikopoulou | 7-6,6-2 |
| ITF Women Loughborough | 2018/02/08 11:25 | Jesika Maleckova v Valentini Grammatikopoulou | 7-6,6-3 |
| ITF Women Loughborough | 2018/02/07 12:15 | Petra Krejsova v Valentini Grammatikopoulou | 5-7,1-6 |
| ITF Women Glasgow | 2018/01/31 10:00 | Valentini Grammatikopoulou v Freya Christie | 4-6,3-6 |
| Australian Open Women Qual | 2018/01/13 09:10 | Lin Zhu v Valentini Grammatikopoulou | 4-6,6-2,7-5 |
| Australian Open Women Qual | 2018/01/11 03:30 | Valentini Grammatikopoulou v Ellen Perez | 6-3,4-6,6-2 |
| ITF Women Playford | 2018/01/04 23:30 | Alexandra Bozovic v Valentini Grammatikopoulou | 7-6,4-6,6-4 |
| ITF Women Playford | 2018/01/04 05:20 | Valentini Grammatikopoulou v Jil Teichmann | 7-6,6-3 |