9‑Nov‑2009 | Knoxville CH | Hard | R32 | 296 | 210 | Ilija Bozoljac [SRB] d. Dimitrov | 6-4 6-4 | | | | | | | | | |
2‑Nov‑2009 | Charlottesville CH | Hard | R16 | 308 | 86 | (1)Michael Russell [USA] d. Dimitrov | 4-6 6-4 6-2 | | | | | | | | | |
2‑Nov‑2009 | Charlottesville CH | Hard | R32 | 308 | 172 | Dimitrov d. Michael Yani [USA] | 7-5 1-6 7-6(3) | | | | | | | | | |
19‑Oct‑2009 | Stockholm | Hard | R32 | 310 | 120 | Jarkko Nieminen [FIN] d. (WC)Dimitrov | 6-0 6-2 | | 0.30 | 2.6% | 7.7% | 41.0% | 62.5% | 30.4% | 0/5 | 0:50 |
12‑Oct‑2009 | Kolding CH | Hard | R32 | 308 | 102 | (1)Jarkko Nieminen [FIN] d. Dimitrov | 6-2 6-7(4) 6-2 | | | | | | | | | |
21‑Sep‑2009 | Trnava CH | Clay | R16 | 290 | 120 | (3)Jan Hajek [CZE] d. Dimitrov | 6-3 6-4 | | | | | | | | | |
21‑Sep‑2009 | Trnava CH | Clay | R32 | 290 | 212 | Dimitrov d. Kamil Capkovic [SVK] | 6-3 6-0 | | | | | | | | | |
14‑Sep‑2009 | Todi CH | Clay | R32 | 255 | 137 | (4)Kevin Anderson [RSA] d. Dimitrov | 6-3 6-4 | | | | | | | | | |
7‑Sep‑2009 | Genova CH | Clay | R32 | 271 | 126 | (7)Daniel Brands [GER] d. (WC)Dimitrov | 6-7(1) 6-4 7-6(2) | | | | | | | | | |
31‑Aug‑2009 | US Open | Hard | Q2 | 271 | 69 | (1)Thomaz Bellucci [BRA] d. Dimitrov | 6-4 6-3 | | | | | | | | | |
31‑Aug‑2009 | US Open | Hard | Q1 | 271 | 287 | Dimitrov d. Tobias Kamke [GER] | 6-3 7-5 | | | | | | | | | |
10‑Aug‑2009 | Istanbul CH | Hard | R16 | 276 | 189 | Martin Fischer [AUT] d. (WC)Dimitrov | 6-4 7-6(4) | | | | | | | | | |
10‑Aug‑2009 | Istanbul CH | Hard | R32 | 276 | 121 | (WC)Dimitrov d. (7)Nicolas Mahut [FRA] | 4-6 7-6(1) 7-6(4) | | | | | | | | | |
3‑Aug‑2009 | Segovia CH | Hard | QF | 310 | 98 | (4)Marcel Granollers [ESP] d. (Q)Dimitrov | 6-4 2-6 7-5 | | | | | | | | | |
3‑Aug‑2009 | Segovia CH | Hard | R16 | 310 | 119 | (Q)Dimitrov d. (7)Roko Karanusic [CRO] | 6-3 6-2 | | | | | | | | | |
3‑Aug‑2009 | Segovia CH | Hard | R32 | 310 | 213 | (Q)Dimitrov d. Jesse Huta Galung [NED] | 7-5 4-6 7-6(4) | | | | | | | | | |
13‑Jul‑2009 | Bastad | Clay | R32 | 326 | 151 | (Q)Guillermo Canas [ARG] d. (WC)Dimitrov | 6-3 7-6(2) | | 0.62 | 4.0% | 4.0% | 62.7% | 61.7% | 39.3% | 6/10 | 1:43 |
22‑Jun‑2009 | Wimbledon | Grass | R128 | 342 | 39 | Igor Kunitsyn [RUS] d. (WC)Dimitrov | 3-6 6-0 3-0 RET | | 0.67 | 4.3% | 8.6% | 57.1% | 55.0% | 33.3% | 8/13 | 1:15 |
8‑Jun‑2009 | Queen's Club | Grass | R32 | 361 | 7 | (3)Gilles Simon [FRA] d. (WC)Dimitrov | 7-6(7) 7-6(5) | | 1.02 | 1.1% | 1.1% | 67.8% | 71.2% | 57.1% | 0/1 | 1:50 |
8‑Jun‑2009 | Queen's Club | Grass | R64 | 361 | 82 | (WC)Dimitrov d. Ivan Navarro [ESP] | 6-4 4-6 6-3 | | 1.21 | 10.1% | 3.8% | 64.6% | 90.2% | 39.3% | 1/2 | 1:37 |
1‑Jun‑2009 | Nottingham CH | Grass | QF | 344 | 131 | (5)Ilija Bozoljac [SRB] d. (LL)Dimitrov | 1-6 6-3 6-4 | | | | | | | | | |
1‑Jun‑2009 | Nottingham CH | Grass | R16 | 344 | 196 | (LL)Dimitrov d. Alex Bogdanovic [GBR] | 4-6 7-5 7-6(5) | | | | | | | | | |
1‑Jun‑2009 | Nottingham CH | Grass | R32 | 344 | 108 | (LL)Dimitrov d. (3)Frank Dancevic [CAN] | 6-4 4-6 6-3 | | | | | | | | | |
18‑May‑2009 | Cremona CH | Hard | QF | 366 | 101 | (1)Benjamin Becker [GER] d. (Q)Dimitrov | 6-4 7-5 | | | | | | | | | |
18‑May‑2009 | Cremona CH | Hard | R16 | 366 | 209 | (Q)Dimitrov d. (5)Blaz Kavcic [SLO] | 6-4 6-2 | | | | | | | | | |
18‑May‑2009 | Cremona CH | Hard | R32 | 366 | 284 | (Q)Dimitrov d. Grzegorz Panfil [POL] | 7-6(1) 6-4 | | | | | | | | | |
4‑May‑2009 | Ramat Hasharon CH | Hard | R32 | 380 | 166 | Prakash Amritraj [IND] d. (WC)Dimitrov | 7-6(3) 6-1 | | | | | | | | | |
27‑Apr‑2009 | Rhodes CH | Hard | R32 | 385 | 126 | (7)Benjamin Becker [GER] d. (WC)Dimitrov | 6-2 6-3 | | | | | | | | | |
20‑Apr‑2009 | Sofia CH | Clay | R32 | 390 | 97 | (2)Steve Darcis [BEL] d. (WC)Dimitrov | 7-6(5) 6-3 | | | | | | | | | |
23‑Mar‑2009 | Khorat CH | Hard | R32 | 389 | 271 | Izak Van Der Merwe [RSA] d. (WC)Dimitrov | 7-5 6-2 | | | | | | | | | |
16‑Mar‑2009 | Bangkok CH | Hard | R16 | 400 | 158 | Danai Udomchoke [THA] d. (WC)Dimitrov | 7-6(6) 7-5 | | | | | | | | | |
16‑Mar‑2009 | Bangkok CH | Hard | R32 | 400 | 1337 | (WC)Dimitrov d. (WC)Peerakit Siributwong [THA] | 6-0 6-3 | | | | | | | | | |
6‑Mar‑2009 | Davis Cup G2 R1: HUN vs BUL | Carpet | RR | 402 | 586 | Dimitrov d. Adam Kellner [HUN] | 7-6(5) 6-4 6-7(5) 7-6(5) | | | | | | | | | |
6‑Mar‑2009 | Davis Cup G2 R1: HUN vs BUL | Carpet | RR | 402 | 307 | Dimitrov d. Attila Balazs [HUN] | 7-6(2) 3-6 6-3 3-6 6-0 | | | | | | | | | |
23‑Feb‑2009 | Besancon CH | Hard | R32 | 407 | 102 | (3)Denis Istomin [UZB] d. (WC)Dimitrov | 3-6 6-2 7-6(3) | | | | | | | | | |
16‑Feb‑2009 | Marseille | Hard | R32 | 401 | 8 | (2)Gilles Simon [FRA] d. (WC)Dimitrov | 4-6 6-3 7-5 | | 0.80 | 3.0% | 2.0% | 57.6% | 68.4% | 47.6% | 6/10 | 2:09 |
9‑Feb‑2009 | Rotterdam | Hard | R16 | 478 | 1 | (1)Rafael Nadal [ESP] d. (WC)Dimitrov | 7-5 3-6 6-2 | | 0.76 | 9.8% | 6.5% | 56.5% | 71.2% | 47.5% | 4/8 | 2:26 |
9‑Feb‑2009 | Rotterdam | Hard | R32 | 478 | 23 | (WC)Dimitrov d. Tomas Berdych [CZE] | 4-6 6-3 6-4 | | 0.91 | 9.8% | 1.0% | 62.7% | 75.0% | 50.0% | 9/10 | 2:08 |
26‑Jan‑2009 | USA F3 | Clay | SF | 493 | 397 | (3)Jesse Witten [USA] d. Dimitrov | 6-3 5-7 6-4 | | | | | | | | | |
26‑Jan‑2009 | USA F3 | Clay | QF | 493 | 392 | Dimitrov d. (1)Eric Nunez [USA] | 6-3 6-2 | | | | | | | | | |
26‑Jan‑2009 | USA F3 | Clay | R16 | 493 | 458 | Dimitrov d. (7)Razvan Sabau [ROU] | 7-6(4) 7-5 | | | | | | | | | |
26‑Jan‑2009 | USA F3 | Clay | R32 | 493 | | Dimitrov d. (WC)Raymond Sarmiento [USA] | 6-2 1-6 7-5 | | | | | | | | | |
19‑Jan‑2009 | USA F2 | Clay | R16 | 493 | 431 | (7)Nikola Ciric [SRB] d. Dimitrov | 5-7 6-2 7-5 | | | | | | | | | |
19‑Jan‑2009 | USA F2 | Clay | R32 | 493 | 914 | Dimitrov d. (Q)Milos Raonic [CAN] | 6-4 6-2 | | | | | | | | | |
12‑Jan‑2009 | USA F1 | Clay | R32 | 492 | 573 | Stefano Ianni [ITA] d. Dimitrov | 6-4 4-6 7-6(5) | | | | | | | | | |