| Wimbledon | 07/03 14:15 | 24 | [73] Andreas Seppi v Guido Pella [26] | 4-6,6-4,6-4,5-7,1-6 | |
| Wimbledon | 07/01 13:35 | 23 | [88] Marius Copil v Guido Pella [26] | 6-7,7-5,3-6,4-6 | |
| ATP - Eastbourne | 06/26 10:00 | 26 | [26] Guido Pella v Taylor Fritz [42] | 4-6,6-3,4-6 | |
| ATP - Halle | 06/18 10:00 | 25 | [24] Guido Pella v David Goffin [33] | 1-6,1-6 | |
| French Open | 05/29 09:00 | 24 | [110] Corentin Moutet v Guido Pella [23] | 6-3,6-1,2-6,7-5 | |
| French Open | 05/27 12:10 | 23 | [101] Guido Andreozzi v Guido Pella [23] | 6-7,4-6,6-1,1-6 | |
| ATP - Rom | 05/14 09:00 | 24 | [52] Taylor Fritz v Guido Pella [21] | 6-3,6-4 | |
| ATP - Madrid | 05/08 11:30 | 25 | [34] Stan Wawrinka v Guido Pella [26] | 6-3,6-4 | |
| ATP - Madrid | 05/07 10:00 | 24 | [26] Guido Pella v Daniil Medvedev [14] | 6-2,1-6,6-3 | |
| ATP - München | 05/03 15:15 | 27 | [26] Guido Pella v Roberto Bautista-Agut [21] | 6-4,4-6,0-6 | |
| ATP - München | 05/02 09:00 | 26 | [26] Guido Pella v Taro Daniel [72] | 6-1,6-7,6-3 | |
| ATP - München | 04/30 12:45 | 25 | [26] Guido Pella v Mischa Zverev [95] | 6-2,6-1 | |
| ATP - Barcelona | 04/26 16:40 | 27 | [5] Dominic Thiem v Guido Pella [28] | 7-5,6-2 | |
| ATP - Barcelona | 04/25 17:35 | 26 | [46] Benoit Paire v Guido Pella [28] | 5-7,3-6 | |
| ATP - Barcelona | 04/24 13:55 | 25 | [28] Guido Pella v Karen Khachanov [13] | 6-2,7-6 | |
| ATP - Barcelona | 04/23 15:10 | 24 | [28] Guido Pella v Joao Sousa [50] | 3-6,7-6,6-2 | |
| ATP - Monte Carlo | 04/19 13:45 | 27 | [35] Guido Pella v Rafael Nadal [2] | 6-7,3-6 | |
| ATP - Monte Carlo | 04/18 09:00 | 26 | [35] Guido Pella v Marco Cecchinato [16] | 6-4,4-6,6-4 | |
| ATP - Monte Carlo | 04/16 10:25 | 25 | [11] Marin Cilic v Guido Pella [35] | 3-6,7-5,1-6 | |
| ATP - Monte Carlo | 04/14 14:55 | 24 | [32] Laslo Djere v Guido Pella [34] | 7-6,2-6,4-6 | |
| ATP - Miami | 03/23 15:00 | 24 | [62] Leonardo Mayer v Guido Pella [32] | 6-2,6-4 | |
| ATP - Indian Wells | 03/12 21:20 | 25 | [9] John Isner v Guido Pella [34] | 6-3,6-4 | |
| ATP - Indian Wells | 03/10 21:15 | 24 | [125] Alex Bolt v Guido Pella [34] | 6-7,6-2,3-6 | |
| ATP Sao Paulo | 03/03 17:30 | 29 | [92] Christian Garin v Guido Pella [48] | 5-7,3-6 | |
| ATP Sao Paulo | 03/02 17:30 | 28 | [48] Guido Pella v Laslo Djere [37] | 7-6,7-6 | |
| ATP Sao Paulo | 03/01 18:50 | 27 | [121] Marco Trungelliti v Guido Pella [48] | 0-6,3-6 | |
| ATP Sao Paulo | 02/27 20:45 | 26 | [111] Roberto Carballes Baena v Guido Pella [48] | 2-6,4-6 | |
| ATP - Rio De Janeiro | 02/19 16:00 | 25 | [46] Guido Pella v Joao Sousa [40] | 4-6,6-3,4-6 | |
| ATP - Buenos Aires | 02/16 17:00 | 28 | [18] Marco Cecchinato v Guido Pella [50] | 6-4,6-2 | |
| ATP - Buenos Aires | 02/15 19:45 | 27 | [50] Guido Pella v Jaume Munar [77] | 6-7,7-6,6-1 |