| ATP - Winston-Salem | 08/23 19:00 | 24 | [59] Jordan Thompson v Guido Pella [84] | 6-1,1-6,6-3 | |
| ATP - Cincinnati | 08/19 19:25 | 26 | [93] Guido Pella v Alexander Zverev [5] | 2-6,3-6 | |
| ATP - Cincinnati | 08/18 15:40 | 25 | [93] Guido Pella v Fabio Fognini [36] | 6-1,7-5 | |
| ATP - Cincinnati | 08/16 00:00 | 24 | [19] David Goffin v Guido Pella [93] | 3-6,3-6 | |
| Wimbledon | 06/30 10:00 | 23 | [9] Matteo Berrettini v Guido Pella [59] | 6-4,3-6,6-4,6-0 | |
| ATP - Mallorca | 06/21 11:30 | 25 | [88] Stefano Travaglia v Guido Pella [62] | 7-5,7-6 | |
| ATP - Halle | 06/15 09:00 | 25 | [62] Guido Pella v Lukas Lacko [214] | 7-6,5-7,1-6 | |
| ATP - Stuttgart | 06/09 09:00 | 25 | [61] Guido Pella v Jordan Thompson [64] | 3-6,4-6 | |
| French Open | 06/02 14:00 | 24 | [84] Marcos Giron v Guido Pella [61] | 7-6,6-1,6-7,6-4 | |
| French Open | 05/30 11:00 | 23 | [59] Guido Pella v Daniel Elahi Galan [106] | 6-3,7-6,7-5 | |
| ATP - Geneva | 05/18 12:50 | 25 | [29] Fabio Fognini v Guido Pella [58] | 6-2,6-2 | |
| ATP - Rom | 05/10 08:00 | 24 | Guido Pella v Marton Fucsovics | Cancelled | |
| ATP - Madrid | 05/04 09:00 | 24 | [55] Guido Pella v Jannik Sinner [18] | Retired | |
| ATP - München | 04/28 09:00 | 26 | [40] John Millman v Guido Pella [55] | Retired | |
| ATP - München | 04/26 12:10 | 25 | [55] Guido Pella v Egor Gerasimov [76] | Retired | |
| ATP - Barcelona | 04/19 13:10 | 24 | [39] Kei Nishikori v Guido Pella [50] | 4-6,7-6,6-2 | |
| ATP - Monte Carlo | 04/13 09:00 | 24 | [48] Guido Pella v Lucas Pouille [86] | 3-6,4-6 | |
| ATP - Cagliari | 04/05 09:00 | 25 | [48] Guido Pella v Egor Gerasimov [80] | 4-6,0-6 | |
| Australian Open | 02/09 00:00 | 23 | [44] Guido Pella v Borna Coric [25] | 3-6,6-7,5-7 | |
| ATP Cup | 02/06 06:30 | 1 | [44] Guido Pella v Yoshihito Nishioka [57] | 6-3,7-6 | |
| ATP Cup | 02/05 23:00 | - | Guido Pella v Yoshihito Nishioka | View | |
| ATP Cup | 02/02 06:30 | 1 | [8] Andrey Rublev v Guido Pella [44] | 6-1,6-2 | |
| French Open | 10/01 12:25 | 24 | [37] Guido Pella v Pablo Carreno-Busta [18] | 3-6,2-6,1-6 | |
| French Open | 09/28 14:30 | 23 | [37] Guido Pella v Salvatore Caruso [85] | 7-6,6-7,7-5,6-4 | |
| ATP - Rom | 09/15 12:40 | 24 | [37] Guido Pella v Denis Shapovalov [14] | 2-6,3-6 | |
| ATP - Kitzbühel | 09/10 13:05 | 26 | [57] Feliciano Lopez v Guido Pella [36] | 7-5,6-7,7-6 | |
| ATP - Kitzbühel | 09/08 15:50 | 25 | [49] Yoshihito Nishioka v Guido Pella [36] | 3-6,0-6 | |
| US Open | 09/01 19:55 | 23 | [36] Guido Pella v Jeffrey John Wolf [138] | 2-6,6-0,3-6,3-6 | |
| ATP - Rio De Janeiro | 02/19 00:20 | 25 | [26] Guido Pella v Thiago Monteiro [88] | 7-5,4-6,6-7 | |
| ATP - Buenos Aires | 02/14 19:10 | 27 | [69] Juan Ignacio Londero v Guido Pella [27] | 6-4,7-6 |