| Challenger Men Doubles: Lyon (France) |
| 15.06.19 11:40 | FT | Bolelli S./Andrea Pellegrino | 0 | 4 | 6 | - | - | - | 23 | ||
| Oswald P./Polasek F. | 2 | 6 | 7 | - | - | - |
| 14.06.19 17:10 | FT | Lopez-P. E./Marrero D. (9) | 0 | 2 | 6 | - | - | - | 21 | ||
| Bolelli S./Andrea Pellegrino | 2 | 6 | 7 | - | - | - |
| 13.06.19 14:40 | FT | Margaroli L./Weissborn T.S. (4) | 0 | 1 | 3 | - | - | - | 16 | ||
| Bolelli S./Andrea Pellegrino | 2 | 6 | 6 | - | - | - |
| 12.06.19 21:05 | FT | Bolelli S./Andrea Pellegrino | 2 | 6 | 6 | - | - | - | 20 | ||
| Gonzales R./Vardhan V. | 0 | 4 | 4 | - | - | - |
| Challenger Men Doubles: Poznan (Poland) |
| 06.06.19 18:40 | FT | Michal Dembek/Mergea F. (wc) | 2 | 7 | 4 | 10 | - | - | 41 | ||
| Bolelli S./Mager G. | 1 | 6 | 6 | 8 | - | - |
| 04.06.19 19:20 | FT | Martos S./Pietro Rondoni | 1 | 2 | 6 | 7 | - | - | 34 | ||
| Bolelli S./Mager G. | 2 | 6 | 3 | 10 | - | - |
| ATP Singles: Roland Garros France |
| 28.05.19 16:10 | FT | Bolelli S. (q) | ITA | 0 | 3 | 4 | 5 | - | - | 31 | |||
| Pouille L. (22) | FRA | 3 | 6 | 6 | 7 | - | - |
| ATP Singles: Roland Garros France Qualification |
| 24.05.19 11:10 | FT | Bolelli S. | ITA | 2 | 6 | 7 | - | - | - | 20 | |||
| Soeda G. | JPN | 0 | 1 | 6 | - | - | - |
| 22.05.19 19:20 | FT | Bolelli S. | ITA | 2 | 6 | 3 | 6 | - | - | 25 | |||
| Koepfer D. | GER | 1 | 1 | 6 | 3 | - | - |
| 20.05.19 18:25 | FT | Majchrzak K. (5) | POL | 0 | 5 | 6 | - | - | - | 25 | |||
| Bolelli S. | ITA | 2 | 7 | 7 | - | - | - |
| ATP Doubles: Rome Italy |
| 13.05.19 15:30 | FT | Kubot L./Melo M. (1) | 2 | 6 | 6 | - | - | - | 19 | ||
| Bolelli S./Seppi A. (wc) | 0 | 3 | 4 | - | - | - |
| Challenger Men Doubles: Aix en Provence (France) |
| 10.05.19 13:10 | FT | Nielsen F./Puetz T. (1) | 2 | 6 | 6 | 10 | - | - | 37 | ||
| Bolelli S./Duran G. (15) | 1 | 7 | 4 | 4 | - | - |
| 09.05.19 12:10 | FT | Cerretani J./Monroe N. | 0 | 3 | 2 | - | - | - | 17 | ||
| Bolelli S./Duran G. (15) | 2 | 6 | 6 | - | - | - |
| Challenger Men Singles: Aix en Provence (France) |
| 08.05.19 15:00 | Canc | Masur D. | - | - | - | - | - | - | - | ||
| Bolelli S. (15) | - | - | - | - | - | - |
| Challenger Men Doubles: Aix en Provence (France) |
| 07.05.19 15:00 | FT | Bolelli S./Duran G. (15) | 2 | 6 | 6 | - | - | - | 18 | ||
| Behar A./Travaglia S. | 0 | 3 | 3 | - | - | - |
| ATP Doubles: Estoril Portugal |
| 29.04.19 17:20 | FT | Bolelli S./Lindstedt R. | 1 | 7 | 6 | 7 | - | - | 43 | ||
| Chardy J./Martin F. | 2 | 6 | 7 | 10 | - | - |
| ATP Singles: Estoril Portugal Qualification |
| 28.04.19 14:10 | FT | Popyrin A. (4) | AUS | 2 | 2 | 6 | 6 | - | - | 27 | |||
| Bolelli S. | ITA | 1 | 6 | 3 | 4 | - | - |
| 27.04.19 14:10 | FT | Bolelli S. | ITA | 2 | 6 | 7 | - | - | - | 21 | |||
| Gerasimov E. (7) | BLR | 0 | 2 | 6 | - | - | - |
| ATP Doubles: Marrakech Morocco |
| 12.04.19 13:10 | FT | Middelkoop M./Nielsen F. | 2 | 6 | 6 | - | - | - | 17 | ||
| Bolelli S./Jaziri M. | 0 | 3 | 2 | - | - | - |
| 10.04.19 17:45 | P2 Ret. | Bolelli S./Jaziri M. | 1 | 6 | 2 | - | - | - | 11 | ||
| Gille S./Vliegen J. | 0 | 2 | 1 | - | - | - |
| 08.04.19 16:55 | P1 Ret. | Puetz T./Venus M. (3) | 1 | 6 | 1 | - | - | - | 14 | ||
| Bolelli S./Jaziri M. | 0 | 3 | 4 | - | - | - |
| Challenger Men Singles: Sophia Antipolis (France) |
| 05.04.19 15:10 | FT | Bolelli S. (10) | 1 | 3 | 6 | 3 | - | - | 27 | ||
| Molleker R. (14) | 2 | 6 | 3 | 6 | - | - |
| 04.04.19 20:30 | FT | Sonego L. (6) | 0 | 6 | 6 | - | - | - | 26 | ||
| Bolelli S. (10) | 2 | 7 | 7 | - | - | - |
| 02.04.19 12:55 | FT | Peter Heller | 0 | 2 | 5 | - | - | - | 20 | ||
| Bolelli S. (10) | 2 | 6 | 7 | - | - | - |
| Challenger Men Singles: Marbella (Spain) |
| 28.03.19 19:15 | FT | Monteiro T. (6) | 2 | 6 | 7 | - | - | - | 23 | ||
| Bolelli S. (9) | 0 | 4 | 6 | - | - | - |
| 27.03.19 16:45 | FT | Hemery C. | 0 | 6 | 2 | - | - | - | 21 | ||
| Bolelli S. (9) | 2 | 7 | 6 | - | - | - |
| Challenger Men Singles: Pau (France) |
| 27.02.19 20:50 | FT | Bourgue M. (wc) | 2 | 7 | 7 | - | - | - | 25 | ||
| Bolelli S. (2) | 0 | 5 | 6 | - | - | - |
| ATP Singles: Marseille France |
| 19.02.19 16:20 | FT | Bolelli S. (q) | ITA | 0 | 4 | 6 | - | - | - | 23 | |||
| Paire B. | FRA | 2 | 6 | 7 | - | - | - |
| ATP Singles: Marseille France Qualification |
| 18.02.19 14:10 | FT | Janvier M. | FRA | 0 | 4 | 5 | - | - | - | 22 | |||
| Bolelli S. | ITA | 2 | 6 | 7 | - | - | - |
| 17.02.19 12:10 | FT | Muller A. (wc) | FRA | 0 | 4 | 4 | - | - | - | 20 | |||
| Bolelli S. (5) | ITA | 2 | 6 | 6 | - | - | - |
| Challenger Men Singles: Cherbourg (France) |
| 14.02.19 18:05 | FT | Moraing M. (12) | 2 | 6 | 7 | - | - | - | 22 | ||
| Bolelli S. (5) | 0 | 4 | 5 | - | - | - |
| 13.02.19 22:15 | FT | Lokoli L. (wc) | 0 | 3 | 3 | - | - | - | 18 | ||
| Bolelli S. (5) | 2 | 6 | 6 | - | - | - |
| ATP Doubles: Sofia Bulgaria |
| 07.02.19 18:05 | FT | Mektic N./Melzer J. | 2 | 6 | 7 | 10 | - | - | 42 | ||
| Bolelli S./Seppi A. | 1 | 7 | 6 | 6 | - | - |
| 05.02.19 15:15 | FT | Bolelli S./Seppi A. | 2 | 6 | 1 | 11 | - | - | 36 | ||
| Inglot D./Skugor F. (2) | 1 | 3 | 6 | 9 | - | - |
| ATP Doubles: Davis Cup World Group Qualification |
| 02.02.19 08:00 | Canc | Bopanna R./Sharan D. | - | - | - | - | - | - | - | ||
| Bolelli S./Cecchinato M. | - | - | - | - | - | - |
| ATP Doubles: Australian Open |
| 17.01.19 03:10 | FT | Marach O./Pavic (1) | 2 | 7 | 6 | 6 | - | - | 31 | ||
| Bolelli S./Seppi A. | 1 | 5 | 7 | 0 | - | - |
| ATP Singles: Australian Open Qualification |
| 09.01.19 02:10 | FT | Ito T. | JPN | 2 | 6 | 3 | 6 | - | - | 27 | |||
| Bolelli S. (25) | ITA | 1 | 3 | 6 | 3 | - | - |
| ATP Doubles: Pune India |
| 04.01.19 14:40 | FT | Bopanna R./Sharan D. (1) | 2 | 6 | 3 | 15 | - | - | 46 | ||
| Bolelli S./Dodig I. (q) | 1 | 3 | 6 | 13 | - | - |
| 03.01.19 13:40 | FT | Bolelli S./Dodig I. (q) | 2 | 6 | 6 | - | - | - | 18 | ||
| Krawietz K./Andreas Mies | 0 | 2 | 4 | - | - | - |
| ATP Singles: Pune India |
| 02.01.19 14:40 | FT | Bolelli S. (q) | ITA | 0 | 5 | 0 | - | - | - | 18 | |||
| Munar J. (7) | ESP | 2 | 7 | 6 | - | - | - |
| ATP Doubles: Pune India |
| 01.01.19 16:20 | FT | Arevalo M./Cerretani J. (3) | 1 | 6 | 5 | 7 | - | - | 39 | ||
| Bolelli S./Dodig I. (q) | 2 | 4 | 7 | 10 | - | - |
| ATP Singles: Pune India |
| 01.01.19 12:40 | FT | Bolelli S. (q) | ITA | 2 | 6 | 6 | - | - | - | 20 | |||
| Istomin D. | UZB | 0 | 4 | 4 | - | - | - |
| ATP Singles: Pune India Qualification |
| 30.12.18 10:40 | FT | Ofner S. | AUT | 0 | 6 | 5 | - | - | - | 25 | |||
| Bolelli S. (5) | ITA | 2 | 7 | 7 | - | - | - |
| 29.12.18 10:40 | FT | Schnur B. | CAN | 0 | 3 | 6 | - | - | - | 22 | |||
| Bolelli S. (5) | ITA | 2 | 6 | 7 | - | - | - |
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