| Hernan Gumy ARG | - | F. Volandri | 6-2 | 6-3 | | | | 1st | 23 Oct 00 | Copa Ericsson Brazil - Sao Paulo | Clay |
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| Fernando Meligeni BRA | - | F. Volandri | 6-1 | 6-2 | | | | 1/4 | 09 Oct 00 | Copa Ericsson Mexico - Guadalajara | Clay |
| F. Volandri | - | Kris Goossens BEL | 6-2 | 6-3 | | | | 2nd | 09 Oct 00 |
| F. Volandri | - | Victor Romero MEX | 6-3 | 6-4 | | | | 1st | 09 Oct 00 |
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| O. S.-Gamez ESP | - | F. Volandri | 7-60 | 6-1 | | | | 1/4 | 25 Sep 00 | Copa Sevilla - Seville | Clay |
| F. Volandri | - | Nicolas Coutelot FRA | 7-5 | 6-3 | | | | 2nd | 25 Sep 00 |
| F. Volandri | - | Juan Giner ESP | 7-65 | 6-1 | | | | 1st | 25 Sep 00 |
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| F. Volandri | - | Hernan Gumy ARG | 6-3 | 6-2 | | | | Fin. | 18 Sep 00 | FILA Challenger Biella - Biella | Clay |
| F. Volandri | - | Olivier Rochus BEL | 0-6 | 6-4 | 6-3 | | | 1/2 | 18 Sep 00 |
| F. Volandri | - | Christophe Rochus BEL | 6-0 | 6-3 | | | | 1/4 | 18 Sep 00 |
| F. Volandri | - | Jacobo Diaz-Ruiz ESP | 4-6 | 6-4 | 6-3 | | | 2nd | 18 Sep 00 |
| F. Volandri | - | Ramon Delgado PAR | 6-1 | 3-0 | Ret. | | | 1st | 18 Sep 00 |
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| Nicolas Coutelot FRA | - | F. Volandri | 6-4 | 6-1 | | | | 1/2 | 04 Sep 00 | DPD Challenger 2000 - Aschaffenburg | Clay |
| F. Volandri | - | Julian Knowle AUT | 6-3 | 7-5 | | | | 1/4 | 04 Sep 00 |
| F. Volandri | - | M. Goellner GER | 0-6 | 6-4 | 7-5 | | | 2nd | 04 Sep 00 |
| F. Volandri | - | Robert Lindstedt SWE | 6-2 | 6-1 | | | | 1st | 04 Sep 00 |
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| Kristian Pless DEN | - | F. Volandri | 6-1 | 6-0 | | | | 1st | 28 Aug 00 | Hungarian Architect Open - Budapest | Clay |
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| R. F.-Gil ESP | - | F. Volandri | 7-67 | 6-1 | | | | 2nd | 21 Aug 00 | Geneva Challenger - Geneva | Clay |
| F. Volandri | - | Stefano Galvani ITA | 3-6 | 6-4 | 6-1 | | | 1st | 21 Aug 00 |
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| Albert Montanes ESP | - | F. Volandri | 6-1 | 6-1 | | | | Fin. | 07 Aug 00 | Podebradka Cup - Prague | Clay |
| F. Volandri | - | Radek Stepanek CZE | 6-3 | 2-6 | 6-2 | | | 1/2 | 07 Aug 00 |
| F. Volandri | - | Michal Tabara CZE | 6-4 | 6-4 | | | | 1/4 | 07 Aug 00 |
| F. Volandri | - | Clemens Trimmel AUT | 6-4 | 6-4 | | | | 2nd | 07 Aug 00 |
| F. Volandri | - | Rogier Wassen NED | 6-75 | 6-0 | 6-2 | | | 1st | 07 Aug 00 |
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| Marzio Martelli ITA | - | F. Volandri | 6-3 | 6-4 | | | | 1st | 31 Jul 00 | LTA Men's Challenger - Wrexham | Hard |
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| Johan Van Herck BEL | - | F. Volandri | 6-4 | 6-2 | | | | 1/4 | 24 Jul 00 | Amer-Wilson Challenger - Tampere | Clay |
| F. Volandri | - | Johan Ortegren SWE | 6-2 | 6-1 | | | | 2nd | 24 Jul 00 |
| F. Volandri | - | Dusan Vemic SRB | 6-4 | 7-65 | | | | 1st | 24 Jul 00 |
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| Igor Kunitsyn RUS | - | F. Volandri | 5-7 | 7-62 | 7-5 | | | 1st | 10 Jul 00 | Warsteiner Grand Prix - Oberstaufen | Clay |
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| Feliciano Lopez ESP | - | F. Volandri | 6-2 | 6-4 | | | | 1st | 26 Jun 00 | Memorial Savigni - Sassuolo | Clay |
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| Jimy Szymanski VEN | - | F. Volandri | 6-3 | 6-0 | | | | 1st | 12 Jun 00 | AXA Open II - Espinho | Clay |
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| Edwin Kempes NED | - | F. Volandri | 6-3 | 6-4 | | | | 1st | 22 May 00 | Whirlpool Open - Budapest | Clay |
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| Mikhail Youzhny RUS | - | F. Volandri | 3-6 | 7-63 | 6-3 | | | 1/2 | 15 May 00 | Samarkand Challenger - Samarkand | Clay |
| F. Volandri | - | Marcello Craca GER | 6-3 | 6-4 | | | | 1/4 | 15 May 00 |
| F. Volandri | - | Oleg Ogorodov UZB | 4-6 | 7-5 | 6-2 | | | 2nd | 15 May 00 |
| F. Volandri | - | Albert Montanes ESP | 6-3 | 6-1 | | | | 1st | 15 May 00 |
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| J. Marin CRC | - | F. Volandri | 6-3 | 6-3 | | | | q1 | 08 May 00 | Italian Open - Rome | Clay |
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| Nicolas Coutelot FRA | - | F. Volandri | 6-4 | 6-1 | | | | Q. | 10 Apr 00 | Grand Prix Hassan II - Casablanca | Clay |
| F. Volandri | - | Noam Behr ISR | 2-6 | 6-3 | 6-0 | | | q2 | 10 Apr 00 |
| F. Volandri | - | Oliver Gross GER | 6-3 | 6-74 | 6-3 | | | q1 | 10 Apr 00 |
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| Marzio Martelli ITA | - | F. Volandri | 7-67 | 6-1 | | | | q1 | 03 Apr 00 | Sardinia Int. Camp. - Cagliari | Clay |
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| Federico Luzzi ITA | - | F. Volandri | 6-2 | 4-6 | 7-62 | | | 1st | 27 Mar 00 | Barletta Citta Della Disfida Open 2000 | Clay |
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| V. Santopadre ITA | - | F. Volandri | 6-3 | 6-4 | | | | 2nd | 13 Mar 00 | AXA Open - Lisbon | Clay |
| F. Volandri | - | Francisco Costa BRA | 3-6 | 6-4 | 6-2 | | | 1st | 13 Mar 00 |
| F. Volandri | - | Stefano Galvani ITA | 6-4 | 6-4 | | | | Q. | 13 Mar 00 |
| F. Volandri | - | Nicolas Coutelot FRA | 7-5 | 1-6 | 7-69 | | | q2 | 13 Mar 00 |
| F. Volandri | - | Fabio Maggi ITA | 4-6 | 6-3 | 6-2 | | | q1 | 13 Mar 00 |
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| D. Scheppingen NED | - | F. Volandri | 6-1 | 6-4 | | | | 2nd | 28 Feb 00 | ATP "Videocon" Challenger - Mumbai | Hard |
| F. Volandri | - | Takahiro Terachi JPN | 6-2 | 6-1 | | | | 1st | 28 Feb 00 |
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| Oren Motevassel USA | - | F. Volandri | 4-1 | Ret. | | | | 1/4 | 21 Feb 00 | Bharat Petroleum Ahmedabad Challenger 2000 | Hard |
| F. Volandri | - | Marcello Craca GER | 6-1 | 6-2 | | | | 2nd | 21 Feb 00 |
| F. Volandri | - | Mustafa Ghouse IND | 6-75 | 6-2 | 6-1 | | | 1st | 21 Feb 00 |
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| Mark Hilton GBR | - | F. Volandri | 4-6 | 6-3 | 6-2 | | | 1st | 14 Feb 00 | LTA Hull Challenger - Hull | Carpet |