Stadium: Center Court Round: 25 Ground: Clay
| Challenger Mestre | 2018/05/24 09:00 | Lorenzo Giustino v Caruana, Liam | 6-1,6-1 |
| Challenger Mestre | 2018/05/22 15:00 | Caruana, Liam v Eremin, Edoardo | 6-2,7-6 |
| ATP Rome Qual | 2018/05/12 09:30 | Benneteau, Julien v Caruana, Liam | 6-2,6-0 |
| ITF USA F10 | 2018/04/10 20:00 | Karue Sell v Caruana, Liam | 6-3,6-4 |
| ITF USA F9 | 2018/04/05 15:00 | Collin Altamirano v Caruana, Liam | 6-2,6-4 |
| ITF USA F9 Qual | 2018/04/03 14:00 | Mitjana, Leny v Caruana, Liam | 6-7,0-6 |
| Challenger Punta Del Este Qual | 2018/02/26 16:10 | Londero, Juan Ignacio v Caruana, Liam | 6-2,6-1 |
| Challenger Punta Del Este Qual | 2018/02/25 18:45 | Arus, Rodrigo v Caruana, Liam | 2-6,3-6 |
| ATP Geneva Qual | 2018/05/19 08:00 | Donati, Matteo v Miladinovic, Marko | 2-6,4-6 |
| Challenger - Rome | 2018/05/08 10:05 | Safranek, Vaclav v Donati, Matteo | 1-6,6-2,6-3 |
| Challenger - Ostrava | 2018/05/05 13:40 | Donati, Matteo v de Greef, Arthur | 6-7,4-6 |
| Challenger - Ostrava | 2018/05/04 12:00 | Donati, Matteo v Andrea Collarini | 5-7,6-3,7-5 |
| Challenger - Ostrava | 2018/05/03 11:25 | Ignatik, Uladzimir v Donati, Matteo | 5-7,3-6 |
| Challenger - Ostrava | 2018/05/01 13:55 | Evan Furness v Donati, Matteo | 2-6,3-6 |
| Challenger - Francavilla | 2018/04/27 14:35 | Casper Ruud v Donati, Matteo | 6-7,6-4,7-5 |
| Challenger - Francavilla | 2018/04/25 14:30 | Mathias Bourgue v Donati, Matteo | 4-6,6-2,4-6 |