Massimo Bertolini (born 30 May 1974) is a retired, Italian professional tennis player.
Bertolini had a career high ATP singles ranking of World No. 329, achieved on 1 May 1995. He also had a career high ATP doubles ranking of World No. 36, achieved on 3 May 2004.
A doubles specialist, Bertolini reached 34 doubles finals across his career with a record of 14 wins and 20 losses. Included among those results, he went 12–14 in ATP Challenger Tour finals as well as winning two ATP Tour titles (2–5 overall record). He also reached two Grand Slam quarter-finals, at the 2001 US Open and the 2003 French Open.
ATP career finals
Doubles: 7 (2 titles, 5 runner-ups)
| 
| Legend |  
| Grand Slam tournaments (0–0) |  
| ATP World Tour Finals (0–0) |  
| ATP World Tour Masters 1000 (0–0) |  
| ATP World Tour 500 Series (0–1) |  
| ATP World Tour 250 Series (2–4) |  | 
| Finals by surface |  
| Hard (0–0) |  
| Clay (2–5) |  
| Grass (0–0) |  | 
| Finals by setting |  
| Outdoor (2–5) |  
| Indoor (0–0) |  | 
| Result | W–L | Date | Tournament | Tier | Surface | Partner | Opponents | Score | 
| Loss | 0–1 | Nov 1998 | Santiago, Chile | World Series | Clay |  Devin Bowen |  Sebastián Prieto 
  Mariano Hood | 6–7, 7–6, 6–7 | 
| Loss | 0–2 | Apr 1999 | Barcelona, Spain | Championship Series | Clay |  Cristian Brandi |  Paul Haarhuis 
  Yevgeny Kafelnikov | 5–7, 3–6 | 
| Loss | 0–3 | May 1999 | Munich, Germany | World Series | Clay |  Cristian Brandi |  Daniel Orsanic 
  Mariano Puerta | 6–7(3–7), 6–3, 6–7(3–7) | 
| Loss | 0–4 | Aug 1999 | Unag, Croatia | World Series | Clay |  Cristian Brandi |  Mariano Puerta 
  Javier Sánchez | 6–3, 2–6, 3–6 | 
| Loss | 0–5 | Jul 2002 | Gstaad, Switzerland | World Series | Clay |  Cristian Brandi | .svg.png) Joshua Eagle 
  David Rikl | 6–7(5–7), 4–6 | 
| Win | 1–5 | May 2003 | Sankt Pölten, Austria | World Series | Clay |  Simon Aspelin |  Sargis Sargsian 
 .svg.png) Nenad Zimonjić | 6–4, 6–7(8–10), 6–3 | 
| Win | 2–5 | Jul 2003 | Båstad, Sweden | World Series | Clay |  Simon Aspelin |  Lucas Arnold Ker 
  Mariano Hood | 6–7(3–7), 6–0, 6–4 | 
ATP Challenger and ITF Futures finals
Doubles: 27 (12–15)
| 
| Legend |  
| ATP Challenger (12–14) |  
| ITF Futures (0–1) |  | 
| Finals by surface |  
| Hard (2–2) |  
| Clay (9–11) |  
| Grass (0–2) |  
| Carpet (1–0) |  | 
| Result | W–L | Date | Tournament | Tier | Surface | Partner | Opponents | Score | 
| Loss | 0–1 | Jul 1994 | Bristol, United Kingdom | Challenger | Grass | .svg.png) Dick Norman |  Pietro Pennisi 
  Alexandru Radulescu | 4–6, 5–7 | 
| Loss | 0–2 | Jul 1995 | Manchester, United Kingdom | Challenger | Grass |  Diego Nargiso |  Tim Henman 
  Mark Petchey | 3–6, 4–6 | 
| Win | 1–2 | Mar 1998 | Cherbourg, France | Challenger | Hard |  Massimo Ardinghi |  Jean-Philippe Fleurian 
  Stéphane Simian | 6–3, 2–6, 6–4 | 
| Win | 2–2 | Apr 1998 | Napoli, Italy | Challenger | Clay |  Devin Bowen |  Gábor Köves 
  Tamer El Sawy | 7–6, 6–2 | 
| Loss | 2–3 | Jul 1998 | Venice, Italy | Challenger | Clay |  Sander Groen | .svg.png) Nebojsa Djordjevic 
  Marcos Ondruska | 6–1, 1–6, 2–6 | 
| Loss | 2–4 | Oct 1998 | Barcelona, Spain | Challenger | Clay |  Cristian Brandi |  José Antonio Conde 
  Javier Sánchez | 6–4, 4–6, 3–6 | 
| Loss | 2–5 | Feb 1999 | Cherbourg, France | Challenger | Hard |  Cristian Brandi | .svg.png) Michael Hill 
 .svg.png) Andrew Painter | 5–7, 6–7 | 
| Loss | 2–6 | Apr 1999 | Napoli, Italy | Challenger | Clay |  Cristian Brandi |  Jack Waite 
  Marcos Ondruska | 4–6, 6–7 | 
| Loss | 2–7 | Jun 2001 | Biella, Italy | Challenger | Clay |  Cristian Brandi |  Andrés Schneiter 
  Enzo Artoni | 6–7(5–7), 6–4, 1–6 | 
| Win | 3–7 | Aug 2001 | Bressanone, Italy | Challenger | Clay |  Cristian Brandi | .svg.png) Stephen Huss 
 .svg.png) Lee Pearson | 7–5, 6–3 | 
| Win | 4–7 | Mar 2002 | Barletta, Italy | Challenger | Clay |  Cristian Brandi |  Renzo Furlan 
  Uros Vico | 4–6, 6–3, 7–6(7–4) | 
| Loss | 4–8 | May 2002 | Italy F3, Verona | Futures | Clay |  Achille Margotto |  Stefano Tarallo 
  Elia Grossi | 2–6, 7–5, 3–6 | 
| Win | 5–8 | Jul 2002 | Mantova, Italy | Challenger | Clay |  Giorgio Galimberti |  Jose-Maria Arnedo 
 .svg.png) Joseph Sirianni | 5–7, 6–2, 7–6(9–7) | 
| Loss | 5–9 | Aug 2002 | San Marino, San Marino | Challenger | Clay |  Cristian Brandi |  Leoš Friedl 
  David Škoch | 2–6, 4–6 | 
| Loss | 5–10 | Oct 2002 | Grenoble, France | Challenger | Hard |  Cristian Brandi | .svg.png) Todd Larkham 
 .svg.png) Michael Tebbutt | 6–4, 3–6, 4–6 | 
| Win | 6–10 | Dec 2002 | Milan, Italy | Challenger | Carpet |  Giorgio Galimberti |  Jonathan Erlich 
  Aleksandar Kitinov | 7–6(7–4), 2–6, 7–6(7–4) | 
| Loss | 6–11 | Mar 2003 | Barletta, Italy | Challenger | Clay |  Giorgio Galimberti |  Sebastián Prieto 
  Sergio Roitman | 3–6, 6–3, 3–6 | 
| Win | 7–11 | Apr 2003 | Napoli, Italy | Challenger | Clay |  Giorgio Galimberti |  Amir Hadad 
 .svg.png) Christophe Rochus | 2–6, 7–5, 6–4 | 
| Win | 8–11 | Aug 2003 | San Marino, San Marino | Challenger | Clay | .svg.png) Tom Vanhoudt |  Federico Browne 
  Dominik Hrbatý | 7–5, 6–7(3–7), 6–2 | 
| Win | 9–11 | Aug 2004 | San Marino, San Marino | Challenger | Clay | .svg.png) Tom Vanhoudt |  Álex López Morón 
  Adrián García | 6–2, 6–4 | 
| Win | 10–11 | Aug 2004 | Trani, Italy | Challenger | Clay |  Álex López Morón |  Jan Vacek 
  Martin Štěpánek | 2–6, 6–4, 6–3 | 
| Loss | 10–12 | Sep 2004 | Genoa, Italy | Challenger | Clay | .svg.png) Tom Vanhoudt |  Emilio Benfele Álvarez 
  Álex López Morón | 3–6, 4–6 | 
| Win | 11–12 | Nov 2004 | Luxembourg, Luxembourg | Challenger | Hard |  Petr Luxa |  Karsten Braasch 
  Michael Kohlmann | 7–6(7–4), 4–6, 6–3 | 
| Loss | 11–13 | Apr 2005 | Napoli, Italy | Challenger | Clay |  Uros Vico | .svg.png) Janko Tipsarević 
  Jiří Vaněk | 6–3, 4–6, 2–6 | 
| Win | 12–13 | Apr 2005 | Olbia, Italy | Challenger | Clay |  Uros Vico |  Alessio di Mauro 
  Tomas Tenconi | 6–4, 6–4 | 
| Loss | 12–14 | Apr 2005 | Monza, Italy | Challenger | Clay |  Uros Vico |  Nicolas Devilder 
  Olivier Patience | 5–7, 4–6 | 
| Loss | 12–15 | Jun 2005 | Braunschweig, Germany | Challenger | Clay | .svg.png) Tom Vanhoudt |  Enzo Artoni 
  Álex López Morón | 7–5, 4–6, 6–7(12–14) | 
Key
| W | F | SF | QF | #R | RR | Q# | DNQ | A | NH | 
(W) winner; (F) finalist; (SF) semifinalist; (QF) quarterfinalist; (#R) rounds 4, 3, 2, 1; (RR) round-robin stage; (Q#) qualification round; (DNQ) did not qualify; (A) absent;  (NH) not held; (SR) strike rate (events won / competed); (W–L) win–loss record.
Doubles
External links