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