Stadium: Court 5 Round: 62 Ground: Clay
| ITF M15 Warmbad-Villach | 2021/08/16 12:30 | Chiari, Leonardo v Ondrej Horak | 3-6,2-6 |
| ITF M25 Bolzano | 2021/08/02 09:15 | Chiari, Leonardo v Federico Marchetti | 1-6,3-6 |
| ITF M25 Casinalbo | 2021/07/04 11:45 | Chiari, Leonardo v Ragazzi, Alessandro | 1-6,2-6 |
| ITF - M15 Sharm El Sheikh | 2020/03/09 08:00 | Uzhylovsky, Vladimir v Chiari, Leonardo | 6-1,6-3 |
| ITF - M15 Sharm El Sheikh | 2020/03/02 08:00 | Chiari, Leonardo v Uzhylovsky, Vladimir | 0-6,0-6 |
| ITF - M15 Monastir | 2020/02/17 08:30 | Chiari, Leonardo v Sai K R Ganta | 4-6,3-6 |
| ITF - M15 Monastir | 2020/02/16 08:00 | Chiari, Leonardo v Affes, Mhamed | 6-1,6-1 |
| ITF M25 Grodzisk Mazowiecki | 2021/08/02 10:00 | Kris Krawcewicz v Alan Bojarski | 0-6,6-2,4-10 |
| ITF M25 Kottingbrunn | 2021/07/19 07:55 | Milos Karol v Kris Krawcewicz | 6-4,6-4 |
| ITF M25 Most | 2021/05/23 08:00 | Kris Krawcewicz v Vojtech Mares | 4-6,5-7 |
| ITF M25 Jablonec Nad Nisou | 2021/05/16 11:30 | Hampel, Lenny v Kris Krawcewicz | 7-5,6-2 |
| ITF M25 Prague | 2021/05/09 11:00 | Kris Krawcewicz v Recek, Dominik | 6-2,5-7,7-10 |
| ITF - M15 Opatija | 2021/03/21 08:00 | Kris Krawcewicz v Francesco Maestrelli | 4-6,2-6 |
| ITF - M15 Rovinj | 2021/03/15 08:00 | Kris Krawcewicz v Gergely Madarasz | 4-6,5-7 |
| ITF - M15 Porec | 2021/03/08 14:00 | Gergely Madarasz v Kris Krawcewicz | 6-2,6-3 |