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.
| 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
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| Hard (0–0)
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| Clay (2–5)
|
| Grass (0–0)
|
|
| Finals by setting
|
| Outdoor (2–5)
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| Indoor (0–0)
|
|
| Result
|
W–L
|
Date
|
Tournament
|
Tier
|
Surface
|
Partner
|
Opponents
|
Score
|
| Loss
|
0–1
|
Nov 1998
|
Santiago, Chile
|
World Series
|
Clay
|
United States Devin Bowen
|
Argentina Sebastián Prieto Argentina Mariano Hood
|
6–7, 7–6, 6–7
|
| Loss
|
0–2
|
Apr 1999
|
Barcelona, Spain
|
Championship Series
|
Clay
|
Italy Cristian Brandi
|
Netherlands Paul Haarhuis Russia Yevgeny Kafelnikov
|
5–7, 3–6
|
| Loss
|
0–3
|
May 1999
|
Munich, Germany
|
World Series
|
Clay
|
Italy Cristian Brandi
|
Argentina Daniel Orsanic Argentina Mariano Puerta
|
6–7(3–7), 6–3, 6–7(3–7)
|
| Loss
|
0–4
|
Aug 1999
|
Unag, Croatia
|
World Series
|
Clay
|
Italy Cristian Brandi
|
Argentina Mariano Puerta Spain Javier Sánchez
|
6–3, 2–6, 3–6
|
| Loss
|
0–5
|
Jul 2002
|
Gstaad, Switzerland
|
World Series
|
Clay
|
Italy Cristian Brandi
|
Australia Joshua Eagle Czech Republic David Rikl
|
6–7(5–7), 4–6
|
| Win
|
1–5
|
May 2003
|
Sankt Pölten, Austria
|
World Series
|
Clay
|
Sweden Simon Aspelin
|
Armenia Sargis Sargsian Socialist Federal Republic of Yugoslavia Nenad Zimonjić
|
6–4, 6–7(8–10), 6–3
|
| Win
|
2–5
|
Jul 2003
|
Båstad, Sweden
|
World Series
|
Clay
|
Sweden Simon Aspelin
|
Argentina Lucas Arnold Ker Argentina Mariano Hood
|
6–7(3–7), 6–0, 6–4
|
| 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
|
Belgium Dick Norman
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Italy Pietro Pennisi Romania Alexandru Radulescu
|
4–6, 5–7
|
| Loss
|
0–2
|
Jul 1995
|
Manchester, United Kingdom
|
Challenger
|
Grass
|
Italy Diego Nargiso
|
United Kingdom Tim Henman United Kingdom Mark Petchey
|
3–6, 4–6
|
| Win
|
1–2
|
Mar 1998
|
Cherbourg, France
|
Challenger
|
Hard
|
Italy Massimo Ardinghi
|
France Jean-Philippe Fleurian France Stéphane Simian
|
6–3, 2–6, 6–4
|
| Win
|
2–2
|
Apr 1998
|
Napoli, Italy
|
Challenger
|
Clay
|
United States Devin Bowen
|
Hungary Gábor Köves Tamer El Sawy
|
7–6, 6–2
|
| Loss
|
2–3
|
Jul 1998
|
Venice, Italy
|
Challenger
|
Clay
|
Netherlands Sander Groen
|
Federal Republic of Yugoslavia Nebojsa Djordjevic South Africa Marcos Ondruska
|
6–1, 1–6, 2–6
|
| Loss
|
2–4
|
Oct 1998
|
Barcelona, Spain
|
Challenger
|
Clay
|
Italy Cristian Brandi
|
Spain José Antonio Conde Spain Javier Sánchez
|
6–4, 4–6, 3–6
|
| Loss
|
2–5
|
Feb 1999
|
Cherbourg, France
|
Challenger
|
Hard
|
Italy Cristian Brandi
|
Australia Michael Hill Australia Andrew Painter
|
5–7, 6–7
|
| Loss
|
2–6
|
Apr 1999
|
Napoli, Italy
|
Challenger
|
Clay
|
Italy Cristian Brandi
|
United States Jack Waite South Africa Marcos Ondruska
|
4–6, 6–7
|
| Loss
|
2–7
|
Jun 2001
|
Biella, Italy
|
Challenger
|
Clay
|
Italy Cristian Brandi
|
Argentina Andrés Schneiter Argentina Enzo Artoni
|
6–7(5–7), 6–4, 1–6
|
| Win
|
3–7
|
Aug 2001
|
Bressanone, Italy
|
Challenger
|
Clay
|
Italy Cristian Brandi
|
Australia Stephen Huss Australia Lee Pearson
|
7–5, 6–3
|
| Win
|
4–7
|
Mar 2002
|
Barletta, Italy
|
Challenger
|
Clay
|
Italy Cristian Brandi
|
Italy Renzo Furlan Italy Uros Vico
|
4–6, 6–3, 7–6(7–4)
|
| Loss
|
4–8
|
May 2002
|
Italy F3, Verona
|
Futures
|
Clay
|
Italy Achille Margotto
|
Italy Stefano Tarallo Italy Elia Grossi
|
2–6, 7–5, 3–6
|
| Win
|
5–8
|
Jul 2002
|
Mantova, Italy
|
Challenger
|
Clay
|
Italy Giorgio Galimberti
|
Argentina Jose-Maria Arnedo Australia Joseph Sirianni
|
5–7, 6–2, 7–6(9–7)
|
| Loss
|
5–9
|
Aug 2002
|
San Marino, San Marino
|
Challenger
|
Clay
|
Italy Cristian Brandi
|
Czech Republic Leoš Friedl Czech Republic David Škoch
|
2–6, 4–6
|
| Loss
|
5–10
|
Oct 2002
|
Grenoble, France
|
Challenger
|
Hard
|
Italy Cristian Brandi
|
Australia Todd Larkham Australia Michael Tebbutt
|
6–4, 3–6, 4–6
|
| Win
|
6–10
|
Dec 2002
|
Milan, Italy
|
Challenger
|
Carpet
|
Italy Giorgio Galimberti
|
Israel Jonathan Erlich North Macedonia Aleksandar Kitinov
|
7–6(7–4), 2–6, 7–6(7–4)
|
| Loss
|
6–11
|
Mar 2003
|
Barletta, Italy
|
Challenger
|
Clay
|
Italy Giorgio Galimberti
|
Argentina Sebastián Prieto Argentina Sergio Roitman
|
3–6, 6–3, 3–6
|
| Win
|
7–11
|
Apr 2003
|
Napoli, Italy
|
Challenger
|
Clay
|
Italy Giorgio Galimberti
|
Israel Amir Hadad Belgium Christophe Rochus
|
2–6, 7–5, 6–4
|
| Win
|
8–11
|
Aug 2003
|
San Marino, San Marino
|
Challenger
|
Clay
|
Belgium Tom Vanhoudt
|
Argentina Federico Browne Slovakia Dominik Hrbatý
|
7–5, 6–7(3–7), 6–2
|
| Win
|
9–11
|
Aug 2004
|
San Marino, San Marino
|
Challenger
|
Clay
|
Belgium Tom Vanhoudt
|
Spain Álex López Morón Chile Adrián García
|
6–2, 6–4
|
| Win
|
10–11
|
Aug 2004
|
Trani, Italy
|
Challenger
|
Clay
|
Spain Álex López Morón
|
Czech Republic Jan Vacek Czech Republic Martin Štěpánek
|
2–6, 6–4, 6–3
|
| Loss
|
10–12
|
Sep 2004
|
Genoa, Italy
|
Challenger
|
Clay
|
Belgium Tom Vanhoudt
|
Spain Emilio Benfele Álvarez Spain Álex López Morón
|
3–6, 4–6
|
| Win
|
11–12
|
Nov 2004
|
Luxembourg, Luxembourg
|
Challenger
|
Hard
|
Czech Republic Petr Luxa
|
Germany Karsten Braasch Germany Michael Kohlmann
|
7–6(7–4), 4–6, 6–3
|
| Loss
|
11–13
|
Apr 2005
|
Napoli, Italy
|
Challenger
|
Clay
|
Italy Uros Vico
|
Serbia and Montenegro Janko Tipsarević Czech Republic Jiří Vaněk
|
6–3, 4–6, 2–6
|
| Win
|
12–13
|
Apr 2005
|
Olbia, Italy
|
Challenger
|
Clay
|
Italy Uros Vico
|
Italy Alessio di Mauro Italy Tomas Tenconi
|
6–4, 6–4
|
| Loss
|
12–14
|
Apr 2005
|
Monza, Italy
|
Challenger
|
Clay
|
Italy Uros Vico
|
France Nicolas Devilder France Olivier Patience
|
5–7, 4–6
|
| Loss
|
12–15
|
Jun 2005
|
Braunschweig, Germany
|
Challenger
|
Clay
|
Belgium Tom Vanhoudt
|
Italy Enzo Artoni Spain 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.