Stadium: Court 4 Round: 29 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2019/11/16 09:00 | Aziz Kijametovic v Andrea Guerrieri | 3-6,1-6 |
| ITF M15 Monastir | 2019/11/14 08:30 | Maxime Pauwels v Andrea Guerrieri | 4-6,4-6 |
| ITF M15 Monastir | 2019/11/13 11:15 | Federico Iannaccone v Andrea Guerrieri | 6-1,5-7,2-6 |
| ITF M25 Santa Margherita | 2019/09/24 13:05 | Andrea Guerrieri v Jacopo Berrettini | 6-2,6-7,3-6 |
| ITF M25 Trieste | 2019/09/03 11:25 | Andrea Guerrieri v Yuta Shimizu | 6-7,6-4,1-6 |
| ITF M25 Trieste | 2019/09/02 07:30 | Andrea Guerrieri v Leonardo Taddia | 6-1,6-3 |
| ITF M15 Santa Cristina | 2019/08/15 08:00 | Pietro Rondoni v Andrea Guerrieri | 6-0,6-4 |
| ITF M15 Santa Cristina | 2019/08/14 11:55 | Patric Prinoth v Andrea Guerrieri | 1-6,1-6 |
| ITF M15 Monastir | 2019/11/16 09:00 | Kristjan Tamm v Daniele Capecchi | 0-6,6-3,6-2 |
| ITF M15 Monastir | 2019/11/15 08:30 | Benjamin Winter Lopez v Kristjan Tamm | 3-6,6-3,1-6 |
| ITF M15 Monastir | 2019/11/14 11:15 | Kristjan Tamm v Ivan Davydov | 6-1,6-4 |
| ITF M15 Monastir | 2019/11/13 12:40 | Egor Noskin v Kristjan Tamm | 6-7,2-6 |
| ITF M15 Monastir | 2019/11/06 08:25 | Kristjan Tamm v Aziz Kijametovic | 6-0,4-6,4-6 |
| ITF M15 Parnu | 2019/10/30 10:10 | Stefan Seifert v Kristjan Tamm | 6-3,3-6,6-4 |
| ITF M15 Sharm El Sheikh | 2019/10/17 08:40 | Naoki Tajima v Kristjan Tamm | 6-2,1-6,6-1 |
| ITF M15 Sharm El Sheikh | 2019/10/16 14:30 | Kalman Boyd v Kristjan Tamm | 7-6,6-7,6-7 |