| 8‑Nov‑2009 | Paris Masters | Hard | F | 16 | 3 | (3)Novak Djokovic [SRB] d. (15)Monfils | 6-2 5-7 7-6(3) | (ch) | 0.80 | 11.3% | 5.7% | 61.3% | 73.8% | 36.6% | 5/10 | 2:44 |
| 8‑Nov‑2009 | Paris Masters | Hard | SF | 16 | 14 | (15)Monfils d. (13)Radek Stepanek [CZE] | 6-4 5-7 6-4 | (ch) | 1.01 | 11.5% | 0.0% | 62.5% | 66.7% | 41.7% | 0/5 | 2:42 |
| 8‑Nov‑2009 | Paris Masters | Hard | QF | 16 | 13 | (15)Monfils d. (12)Marin Cilic [CRO] | 3-6 6-4 6-4 | | 0.96 | 14.1% | 0.0% | 66.3% | 78.7% | 45.2% | 4/6 | 2:22 |
| 8‑Nov‑2009 | Paris Masters | Hard | R16 | 16 | 49 | (15)Monfils d. Julien Benneteau [FRA] | 6-4 6-3 | | 1.08 | 22.2% | 0.0% | 68.1% | 77.6% | 47.8% | 6/6 | 1:23 |
| 8‑Nov‑2009 | Paris Masters | Hard | R32 | 16 | 179 | (15)Monfils d. (Q)David Guez [FRA] | 6-4 7-5 | | 1.30 | 16.2% | 4.4% | 66.2% | 84.4% | 39.1% | 3/4 | 1:33 |
| 2‑Nov‑2009 | Valencia | Hard | R16 | 16 | 47 | Guillermo Garcia Lopez [ESP] d. (6)Monfils | 6-2 7-5 | | 0.70 | 1.3% | 5.3% | 66.7% | 56.0% | 56.0% | 5/8 | 1:37 |
| 2‑Nov‑2009 | Valencia | Hard | R32 | 16 | 82 | (6)Monfils d. (WC)Marcel Granollers [ESP] | 6-4 6-2 | | 1.16 | 2.8% | 1.4% | 53.5% | 68.4% | 45.5% | 8/10 | 1:11 |
| 26‑Oct‑2009 | Vienna | Hard | QF | 15 | 46 | Janko Tipsarevic [SRB] d. (3)Monfils | 6-4 6-7(8) 6-3 | | 0.86 | 7.9% | 3.0% | 64.4% | 75.4% | 47.2% | 7/10 | 2:12 |
| 26‑Oct‑2009 | Vienna | Hard | R16 | 15 | 113 | (3)Monfils d. Jan Hajek [CZE] | 6-1 2-6 6-4 | | 1.24 | 10.7% | 4.0% | 69.3% | 71.2% | 52.2% | 1/3 | 1:31 |
| 26‑Oct‑2009 | Vienna | Hard | R32 | 15 | 47 | (3)Monfils d. Guillermo Garcia Lopez [ESP] | 7-5 6-4 | | 1.71 | 12.1% | 1.7% | 60.3% | 85.7% | 69.6% | 2/2 | 1:22 |
| 11‑Oct‑2009 | Shanghai Masters | Hard | R16 | 14 | 37 | Ivan Ljubicic [CRO] d. (11)Monfils | 6-2 3-0 RET | | 0.37 | 0.0% | 5.1% | 84.6% | 48.5% | 33.3% | 1/5 | 0:37 |
| 11‑Oct‑2009 | Shanghai Masters | Hard | R32 | 14 | 23 | (11)Monfils d. Lleyton Hewitt [AUS] | 4-6 6-4 6-2 | | 1.14 | 9.2% | 9.2% | 60.5% | 67.4% | 43.3% | 3/7 | 2:04 |
| 11‑Oct‑2009 | Shanghai Masters | Hard | R64 | 14 | 35 | (11)Monfils d. Paul Henri Mathieu [FRA] | 6-2 6-2 | | 1.91 | 15.9% | 6.8% | 65.9% | 82.8% | 60.0% | 1/1 | 0:55 |
| 5‑Oct‑2009 | Tokyo | Hard | SF | 13 | 7 | (2)Jo Wilfried Tsonga [FRA] d. (4)Monfils | 6-3 6-3 | | 0.34 | 6.6% | 4.9% | 67.2% | 70.7% | 30.0% | 4/7 | 0:56 |
| 5‑Oct‑2009 | Tokyo | Hard | QF | 13 | 23 | (4)Monfils d. (7)Stan Wawrinka [SUI] | 2-6 6-3 6-4 | | 0.92 | 9.6% | 3.2% | 67.0% | 71.4% | 48.4% | 4/6 | 1:53 |
| 5‑Oct‑2009 | Tokyo | Hard | R16 | 13 | 100 | (4)Monfils d. (Q)Marco Chiudinelli [SUI] | 7-6(5) 6-3 | | 1.27 | 15.2% | 1.5% | 56.1% | 78.4% | 55.2% | 4/5 | 1:26 |
| 5‑Oct‑2009 | Tokyo | Hard | R32 | 13 | 160 | (4)Monfils d. (Q)Marsel Ilhan [TUR] | 6-2 6-4 | | 1.21 | 24.2% | 0.0% | 75.8% | 70.2% | 53.3% | 5/5 | 1:06 |
| 28‑Sep‑2009 | Kuala Lumpur | Hard | QF | 13 | 8 | (1)Nikolay Davydenko [RUS] d. (5)Monfils | 6-3 6-3 | | 0.59 | 11.9% | 6.8% | 57.6% | 61.8% | 36.0% | 5/9 | 1:14 |
| 28‑Sep‑2009 | Kuala Lumpur | Hard | R16 | 13 | 49 | (5)Monfils d. Martin Vassallo Arguello [ARG] | 6-4 6-2 | | 1.55 | 7.0% | 1.8% | 59.6% | 73.5% | 60.9% | 1/2 | 1:33 |
| 28‑Sep‑2009 | Kuala Lumpur | Hard | R32 | 13 | 94 | (5)Monfils d. Denis Istomin [UZB] | 7-6(3) 7-6(2) | | 1.35 | 12.2% | 2.7% | 64.9% | 77.1% | 57.7% | 0/3 | 1:36 |
| 21‑Sep‑2009 | Metz | Hard | F | 13 | 23 | (1)Monfils d. (2)Philipp Kohlschreiber [GER] | 7-6(1) 3-6 6-2 | | 1.57 | 16.7% | 2.4% | 59.5% | 88.0% | 55.9% | 3/4 | 2:13 |
| 21‑Sep‑2009 | Metz | Hard | SF | 13 | 47 | (1)Monfils d. Richard Gasquet [FRA] | 6-4 6-3 | | 1.80 | 26.0% | 2.0% | 60.0% | 90.0% | 55.0% | 4/4 | 1:21 |
| 21‑Sep‑2009 | Metz | Hard | QF | 13 | 55 | (1)Monfils d. Janko Tipsarevic [SRB] | 6-1 4-2 RET | | 2.00 | 20.0% | 0.0% | 62.5% | 88.0% | 53.3% | 0/0 | 0:46 |
| 21‑Sep‑2009 | Metz | Hard | R16 | 13 | 1147 | (1)Monfils d. (WC)Sebastien Grosjean [FRA] | 6-1 6-1 | | 1.57 | 20.0% | 2.0% | 56.0% | 78.6% | 45.5% | 6/7 | 1:06 |
| 18‑Sep‑2009 | Davis Cup WG PO: NED vs FRA | Clay | RR | 13 | 122 | Thiemo De Bakker [NED] d. Monfils | 6-3 5-7 6-3 6-4 | | | | | | | | | |
| 31‑Aug‑2009 | US Open | Hard | R16 | 13 | 3 | (3)Rafael Nadal [ESP] d. (13)Monfils | 6-7(3) 6-3 6-1 6-3 | | 0.69 | 10.2% | 3.7% | 61.1% | 69.7% | 35.7% | 6/14 | 2:45 |
| 31‑Aug‑2009 | US Open | Hard | R32 | 13 | 47 | (13)Monfils d. Jose Acasuso [ARG] | 6-3 6-4 1-0 RET | | 1.52 | 16.9% | 1.7% | 69.5% | 80.5% | 61.1% | 1/1 | 1:25 |
| 31‑Aug‑2009 | US Open | Hard | R64 | 13 | 40 | (13)Monfils d. Andreas Beck [GER] | 6-3 7-5 6-3 | | 1.28 | 17.2% | 3.0% | 61.6% | 77.0% | 50.0% | 2/3 | 1:58 |
| 31‑Aug‑2009 | US Open | Hard | R128 | 13 | 34 | (13)Monfils d. Jeremy Chardy [FRA] | 6-1 6-4 6-3 | | 1.46 | 15.8% | 0.0% | 57.9% | 81.8% | 50.0% | 3/4 | 1:35 |
| 16‑Aug‑2009 | Cincinnati Masters | Hard | R64 | 13 | 29 | Ivo Karlovic [CRO] d. (13)Monfils | 6-4 6-7(5) 7-6(2) | | 0.81 | 7.2% | 0.9% | 66.7% | 77.0% | 62.2% | 5/6 | 2:11 |
| 10‑Aug‑2009 | Canada Masters | Hard | R32 | 13 | 29 | (Q)Juan Carlos Ferrero [ESP] d. (13)Monfils | 6-3 7-6(7) | | 0.73 | 16.7% | 1.5% | 62.1% | 73.2% | 40.0% | 0/2 | 1:45 |
| 10‑Aug‑2009 | Canada Masters | Hard | R64 | 13 | 61 | (13)Monfils d. Marat Safin [RUS] | 6-2 3-6 6-2 | | 1.42 | 13.7% | 1.4% | 65.8% | 75.0% | 56.0% | 0/2 | 1:49 |
| 8‑Jun‑2009 | Queen's Club | Grass | R16 | 14 | 73 | Steve Darcis [BEL] d. (4)Monfils | W/O | | | | | | | | | |
| 8‑Jun‑2009 | Queen's Club | Grass | R32 | 14 | 74 | (4)Monfils d. Andrey Golubev [KAZ] | 6-3 3-6 7-6(5) | | 1.33 | 4.5% | 3.4% | 70.8% | 77.8% | 61.5% | 3/5 | 1:52 |
| 25‑May‑2009 | Roland Garros | Clay | QF | 10 | 2 | (2)Roger Federer [SUI] d. (11)Monfils | 7-6(6) 6-2 6-4 | (ch) | 0.66 | 6.7% | 1.0% | 58.1% | 67.2% | 50.0% | 2/5 | 2:10 |
| 25‑May‑2009 | Roland Garros | Clay | R16 | 10 | 6 | (11)Monfils d. (6)Andy Roddick [USA] | 6-4 6-2 6-3 | (ch) | 1.44 | 20.5% | 3.6% | 59.0% | 75.5% | 58.8% | 9/10 | 1:51 |
| 25‑May‑2009 | Roland Garros | Clay | R32 | 10 | 26 | (11)Monfils d. (24)Jurgen Melzer [AUT] | 6-2 4-6 6-3 6-1 | | 1.24 | 10.7% | 0.9% | 64.3% | 73.6% | 47.5% | 6/8 | 2:17 |
| 25‑May‑2009 | Roland Garros | Clay | R64 | 10 | 99 | (11)Monfils d. (Q)Victor Crivoi [ROU] | 6-4 6-3 6-3 | | 1.45 | 4.7% | 0.0% | 68.6% | 76.3% | 63.0% | 2/2 | 1:45 |
| 25‑May‑2009 | Roland Garros | Clay | R128 | 10 | 83 | (11)Monfils d. Bobby Reynolds [USA] | 6-2 6-3 6-1 | | 2.23 | 7.5% | 0.0% | 62.7% | 83.3% | 68.0% | 2/2 | 1:29 |
| 12‑Apr‑2009 | Monte Carlo Masters | Clay | R64 | 10 | 56 | Janko Tipsarevic [SRB] d. (9)Monfils | 6-3 6-1 | | 0.64 | 3.8% | 7.7% | 50.0% | 53.8% | 34.6% | 3/8 | 1:07 |
| 25‑Mar‑2009 | Miami Masters | Hard | R16 | 10 | 6 | (5)Andy Roddick [USA] d. (9)Monfils | 7-6(2) 6-4 | | 0.60 | 13.2% | 6.6% | 61.8% | 72.3% | 41.4% | 3/5 | 1:37 |
| 25‑Mar‑2009 | Miami Masters | Hard | R32 | 10 | 23 | (9)Monfils d. (22)Marat Safin [RUS] | 5-7 7-5 7-6(3) | | 1.10 | 11.8% | 1.8% | 53.6% | 71.2% | 54.9% | 8/12 | 2:53 |
| 25‑Mar‑2009 | Miami Masters | Hard | R64 | 10 | 241 | (9)Monfils d. (Q)Michael Russell [USA] | 6-2 6-7(5) 6-3 | | 1.49 | 10.5% | 7.0% | 57.0% | 93.9% | 56.8% | 5/5 | 1:47 |
| 12‑Mar‑2009 | Indian Wells Masters | Hard | R64 | 9 | 147 | (WC)John Isner [USA] d. (9)Monfils | 6-7(5) 6-1 6-4 | | 0.58 | 8.5% | 5.3% | 63.8% | 75.0% | 47.1% | 6/9 | 1:58 |
| 23‑Feb‑2009 | Acapulco | Clay | F | 10 | 21 | (4)Nicolas Almagro [ESP] d. (2)Monfils | 6-4 6-4 | | 0.65 | 11.9% | 3.4% | 59.3% | 77.1% | 37.5% | 5/8 | 1:17 |
| 23‑Feb‑2009 | Acapulco | Clay | SF | 10 | 43 | (2)Monfils d. (5)Jose Acasuso [ARG] | 6-3 6-4 | | 1.66 | 18.6% | 3.4% | 64.4% | 89.5% | 52.4% | 4/4 | 1:25 |
| 23‑Feb‑2009 | Acapulco | Clay | QF | 10 | 110 | (2)Monfils d. Leonardo Mayer [ARG] | 6-3 6-7(4) 4-1 RET | | 1.26 | 8.9% | 4.4% | 62.2% | 75.0% | 64.7% | 3/3 | 2:06 |
| 23‑Feb‑2009 | Acapulco | Clay | R16 | 10 | 68 | (2)Monfils d. Thomaz Bellucci [BRA] | 7-6(4) 6-7(5) 6-1 | | 1.39 | 6.2% | 2.1% | 63.9% | 80.6% | 60.0% | 2/3 | 2:24 |
| 23‑Feb‑2009 | Acapulco | Clay | R32 | 10 | 139 | (2)Monfils d. (Q)Olivier Patience [FRA] | 7-6(4) 6-4 | | 1.75 | 27.4% | 3.2% | 51.6% | 96.9% | 60.0% | 2/3 | 1:43 |
| 16‑Feb‑2009 | Marseille | Hard | R32 | 11 | 34 | Paul Henri Mathieu [FRA] d. (3)Monfils | 4-6 6-4 7-5 | | 1.19 | 29.2% | 6.7% | 52.8% | 91.5% | 47.6% | 1/3 | 2:10 |
| 9‑Feb‑2009 | Rotterdam | Hard | SF | 12 | 1 | (1)Rafael Nadal [ESP] d. (5)Monfils | 6-4 6-4 | | 0.75 | 15.6% | 3.1% | 57.8% | 70.3% | 40.7% | 3/6 | 1:42 |
| 9‑Feb‑2009 | Rotterdam | Hard | QF | 12 | 50 | (5)Monfils d. Julien Benneteau [FRA] | 7-6(4) 6-1 | | 1.20 | 11.7% | 3.3% | 66.7% | 75.0% | 55.0% | 1/2 | 1:17 |
| 9‑Feb‑2009 | Rotterdam | Hard | R16 | 12 | 51 | (5)Monfils d. Michael Llodra [FRA] | 6-4 6-4 | | 1.27 | 12.3% | 1.8% | 70.2% | 77.5% | 64.7% | 1/1 | 1:12 |
| 9‑Feb‑2009 | Rotterdam | Hard | R32 | 12 | 154 | (5)Monfils d. (Q)Stephane Bohli [SUI] | 6-4 1-0 RET | | 0.95 | 5.6% | 5.6% | 44.4% | 81.3% | 50.0% | 1/1 | 0:42 |
| 19‑Jan‑2009 | Australian Open | Hard | R16 | 13 | 8 | (6)Gilles Simon [FRA] d. (12)Monfils | 6-4 2-6 6-1 RET | | 0.86 | 1.1% | 3.4% | 56.2% | 60.0% | 41.0% | 5/10 | 1:59 |
| 19‑Jan‑2009 | Australian Open | Hard | R32 | 13 | 18 | (12)Monfils d. (17)Nicolas Almagro [ESP] | 6-4 6-3 7-5 | | 1.21 | 11.9% | 0.0% | 66.3% | 76.1% | 47.1% | 4/5 | 2:09 |
| 19‑Jan‑2009 | Australian Open | Hard | R64 | 13 | 183 | (12)Monfils d. Stefan Koubek [AUT] | 6-4 6-4 3-6 6-2 | | 1.14 | 16.2% | 5.7% | 61.9% | 73.8% | 62.5% | 4/6 | 2:05 |
| 19‑Jan‑2009 | Australian Open | Hard | R128 | 13 | 71 | (12)Monfils d. Martin Vassallo Arguello [ARG] | 6-1 6-3 7-5 | | 1.38 | 9.8% | 8.7% | 51.1% | 83.0% | 42.2% | 6/9 | 2:25 |
| 5‑Jan‑2009 | Doha | Hard | SF | 13 | 8 | (4)Andy Roddick [USA] d. (5)Monfils | 7-6(1) 3-6 6-3 | | 0.98 | 12.8% | 2.3% | 66.3% | 73.7% | 51.7% | 2/5 | 2:02 |
| 5‑Jan‑2009 | Doha | Hard | QF | 13 | 1 | (5)Monfils d. (1)Rafael Nadal [ESP] | 6-4 6-4 | | 1.36 | 12.3% | 0.0% | 70.2% | 82.5% | 35.3% | 0/1 | 1:29 |
| 5‑Jan‑2009 | Doha | Hard | R16 | 13 | 72 | (5)Monfils d. Nicolas Devilder [FRA] | 7-5 7-6(4) | | 1.28 | 11.4% | 0.0% | 60.8% | 75.0% | 51.6% | 2/4 | 2:07 |
| 5‑Jan‑2009 | Doha | Hard | R32 | 13 | 79 | (5)Monfils d. Jan Hernych [CZE] | 6-2 6-2 | | 1.72 | 18.0% | 4.0% | 70.0% | 77.1% | 40.0% | 2/3 | 0:55 |
