Janko Tipsarevic | ||||||||||||||||||||||||
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| Valencia Open 500 | ||
| Surface: Clay | Date: Nov. 2 - Nov. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Victor Hanescu | Win | 6-4, 6-3 |
| Second Round | Fernando Verdasco | Loss | 3-6, 3-6 |
| Bank Austria Tennis Trophy | ||
| Surface: Hard | Date: Oct. 26 - Nov. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Isner | Win | 7-6 (7-4), 6-4 |
| Second Round | Michael Berrer | Win | 7-6 (7-3), 6-1 |
| Quarter Finals | Gael Monfils | Win | 6-4, 6-7 (8-10), 6-3 |
| Semi Finals | Jurgen Melzer | Loss | 6-4, 6-7 (5-7), 4-6 |
| Kremlin Cup | ||
| Surface: Supreme | Date: Oct. 19 - Oct. 25 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Koellerer | Win | 6-4, 6-3 |
| Second Round | Christophe Rochus | Win | 6-4, 2-1, Retired |
| Quarter Finals | Robby Ginepri | Win | 6-3, 6-3 |
| Semi Finals | Illya Marchenko | Win | 6-1, 6-4 |
| Final | Mikhail Youzhny | Loss | 7-6 (7-5), 0-6, 4-6 |
| Open de Moselle | ||
| Surface: Hard | Date: Sep. 21 - Sep. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Arnaud Clement | Win | 6-4, 6-4 |
| Second Round | Ivan Ljubicic | Win | 6-4, 7-6 (7-3) |
| Quarter Finals | Gael Monfils | Loss | 1-6, 2-4 Retired |
| US Open | ||
| Surface: Hard | Date: Aug. 31 - Sep. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Florent Serra | Loss | 6-7 (8-10), 6-7 (5-7), 6-7 (5-7) |
| Pilot Pen Tennis Presented By Schick | ||
| Surface: Hard | Date: Aug. 23 - Aug. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fabio Fognini | Win | 7-5, 2-0 Retired |
| Second Round | Victor Hanescu | Loss | 4-6, 7-6 (10-8), 3-6 |
| International German Open | ||
| Surface: Red Clay | Date: Jul. 20 - Jul. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Simon Greul | Loss | 6-2, 3-6, 3-6 |
| Mercedes Cup | ||
| Surface: Clay | Date: Jul. 13 - Jul. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Oscar Hernandez | Loss | 4-6, 4-6 Retired |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 22 - Jul. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan Hernych | Win | 6-4, 6-4, 7-6 (7-4) |
| Second Round | Mardy Fish | Loss | 4-6, 6-3, 1-6, 4-6 |
| AEGON International | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Paul-Henri Mathieu | Win | 6-4, 6-2 |
| Second Round | Brydan Klein | Win | 7-6 (7-5), 6-1 |
| Quarter Finals | Guillermo Garcia-Lopez | Loss | 4-6, 6-3, 3-6 |
| AEGON Championships | ||
| Surface: Grass | Date: Jun. 8 - Jun. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Mahut | Loss | 0-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 24 - Jun. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Montanes | Win | 3-6, 7-6 (7-3), 7-6 (7-5), 6-4 |
| Second Round | Feliciano Lopez | Win | 6-7 (9-11), 6-4, 7-6 (7-4), 6-3 |
| Third Round | Andy Murray | Loss | 6-7 (3-7), 3-6 Retired |
| Mutua Madrilena Masters Madrid | ||
| Surface: Clay | Date: May 9 - May 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mardy Fish | Loss | 6-7 (3-7), 4-6 |
| Serbia Open 2009 | ||
| Surface: Clay | Date: May 4 - May 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sergio Roitman | Win | 7-5, 6-2 |
| Second Round | Novak Djokovic | Loss | 2-6, 6-4, 0-6 |
| Internazionali BNL d Italia | ||
| Surface: Red Clay | Date: Apr. 27 - May 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jose Acasuso | Win | 6-3, 6-4 |
| Second Round | Fernando Gonzalez | Loss | 4-6, 4-6 |
| Barcelona Open Banco Sabadell | ||
| Surface: Clay | Date: Apr. 20 - Apr. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Montanes | Win | 6-4, 7-6 (7-1) |
| Second Round | Radek Stepanek | Loss | 6-7 (2-7), 0-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 12 - Apr. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Win | 6-3, 6-1 |
| Second Round | Simone Bolelli | Loss | 5-7, 3-6 |
| Sony Ericsson Open | ||
| Surface: Hard | Date: Mar. 25 - Apr. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jose Acasuso | Win | 6-4, 4-6, 6-3 |
| Second Round | Jurgen Melzer | Win | 6-4, 6-3 |
| Third Round | Juan Martin del Potro | Loss | 4-6, 1-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 11 - Mar. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thomaz Bellucci | Loss | 7-5, 5-7, 2-6 |
| The Dubai Tennis Championships | ||
| Surface: Hard | Date: Feb. 23 - Feb. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marin Cilic | Loss | 6-2, 6-7 (3-7), 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 18 - Feb. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Oscar Hernandez | Win | 4-6, 6-1, 6-3, 4-6, 6-0 |
| Second Round | Marin Cilic | Loss | 2-6, 3-6, 6-4, 3-6 |
| Medibank International | ||
| Surface: Hard | Date: Jan. 11 - Jan. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mardy Fish | Win | 6-4, 3-6, 6-4 |
| Second Round | Lleyton Hewitt | Loss | 5-7, 4-6 |
| Chennai Open | ||
| Surface: Hard | Date: Jan. 5 - Jan. 11 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Pablo Andujar | Win | 6-3, 6-2 |
| Second Round | Dudi Sela | Win | 7-6 (7-3), 6-4 |
| Quarter Finals | Marin Cilic | Loss | 4-6, 6-0, 4-6 |
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