2‑Nov‑2009 | Charlottesville CH | Hard | QF | 370 | 116 | (3)Somdev Devvarman [IND] d. Middelkoop | 6-3 6-4 | | | | | | | | | |
2‑Nov‑2009 | Charlottesville CH | Hard | R16 | 370 | 373 | Middelkoop d. Ryan Harrison [USA] | 1-6 6-3 6-2 | | | | | | | | | |
2‑Nov‑2009 | Charlottesville CH | Hard | R32 | 370 | 171 | Middelkoop d. (8)Jesse Witten [USA] | 6-3 6-4 | | | | | | | | | |
26‑Oct‑2009 | Lyon | Hard | Q2 | 349 | 371 | Charles Antoine Brezac [FRA] d. Middelkoop | 6-4 6-4 | | | | | | | | | |
26‑Oct‑2009 | Lyon | Hard | Q1 | 349 | 222 | Middelkoop d. (7)Giovanni Lapentti [ECU] | 7-6(6) 7-5 | | | | | | | | | |
19‑Oct‑2009 | Orleans CH | Hard | R32 | 357 | 36 | (1)Jeremy Chardy [FRA] d. (Q)Middelkoop | 4-6 7-6(1) 6-4 | | | | | | | | | |
12‑Oct‑2009 | Tashkent CH | Hard | R32 | 310 | 112 | (8)Sergiy Stakhovsky [UKR] d. Middelkoop | 2-6 6-2 7-5 | | | | | | | | | |
28‑Sep‑2009 | Napoli2 CH | Clay | R32 | 298 | 152 | Pere Riba [ESP] d. (Q)Middelkoop | 6-3 6-1 | | | | | | | | | |
14‑Sep‑2009 | Banja Luka CH | Clay | QF | 316 | 306 | Dusan Lojda [CZE] d. Middelkoop | W/O | | | | | | | | | |
14‑Sep‑2009 | Banja Luka CH | Clay | R16 | 316 | 249 | Middelkoop d. Benjamin Balleret [MON] | 6-4 6-3 | | | | | | | | | |
14‑Sep‑2009 | Banja Luka CH | Clay | R32 | 316 | 217 | Middelkoop d. (8)Kamil Capkovic [SVK] | 6-0 1-1 RET | | | | | | | | | |
7‑Sep‑2009 | Alphen aan den Rijn CH | Clay | QF | 282 | 112 | (2)Michael Russell [USA] d. (WC)Middelkoop | 6-3 2-6 6-3 | | | | | | | | | |
7‑Sep‑2009 | Alphen aan den Rijn CH | Clay | R16 | 282 | 525 | (WC)Middelkoop d. (Q)Timo Nieminen [FIN] | 7-5 7-6(6) | | | | | | | | | |
7‑Sep‑2009 | Alphen aan den Rijn CH | Clay | R32 | 282 | 176 | (WC)Middelkoop d. Michael Lammer [SUI] | 3-6 6-3 6-2 | | | | | | | | | |
31‑Aug‑2009 | Brasov CH | Clay | R16 | 282 | 151 | (1)Thiemo De Bakker [NED] d. Middelkoop | 6-4 5-7 7-5 | | | | | | | | | |
31‑Aug‑2009 | Brasov CH | Clay | R32 | 282 | 394 | Middelkoop d. Grzegorz Panfil [POL] | 6-3 6-1 | | | | | | | | | |
24‑Aug‑2009 | Manerbio CH | Clay | R32 | 275 | 344 | (Q)Leonardo Tavares [POR] d. Middelkoop | 5-7 7-5 6-2 | | | | | | | | | |
17‑Aug‑2009 | Trani CH | Clay | R16 | 287 | 320 | Enrico Burzi [ITA] d. Middelkoop | 6-4 6-3 | | | | | | | | | |
17‑Aug‑2009 | Trani CH | Clay | R32 | 287 | 132 | Middelkoop d. (5)Sebastian Decoud [ARG] | 6-4 7-6(4) | | | | | | | | | |
27‑Jul‑2009 | Saransk CH | Clay | R16 | 301 | 670 | (Q)Mikhail Ledovskikh [RUS] d. Middelkoop | 6-4 6-3 | | | | | | | | | |
27‑Jul‑2009 | Saransk CH | Clay | R32 | 301 | 490 | Middelkoop d. (LL)Artem Sitak [NZL] | 6-4 6-2 | | | | | | | | | |
20‑Jul‑2009 | Penza CH | Hard | QF | 306 | 169 | (2)Mikhail Kukushkin [KAZ] d. (8)Middelkoop | 6-0 7-6(6) | | | | | | | | | |
20‑Jul‑2009 | Penza CH | Hard | R16 | 306 | 373 | (8)Middelkoop d. Konstantin Kravchuk [RUS] | 6-2 6-3 | | | | | | | | | |
20‑Jul‑2009 | Penza CH | Hard | R32 | 306 | | (8)Middelkoop d. (WC)Vladislav Dubinsky [RUS] | 6-4 6-3 | | | | | | | | | |
6‑Jul‑2009 | Pozoblanco CH | Hard | R16 | 277 | 98 | (4)Thiago Alves [BRA] d. Middelkoop | 6-2 2-6 6-1 | | | | | | | | | |
6‑Jul‑2009 | Pozoblanco CH | Hard | R32 | 277 | 228 | Middelkoop d. Pavel Snobel [CZE] | 7-6(7) 4-6 6-1 | | | | | | | | | |
22‑Jun‑2009 | Netherlands F3 | Clay | QF | 291 | 568 | Leonardo Azzaro [ITA] d. (1)Middelkoop | 7-6(6) 4-6 7-6(10) | | | | | | | | | |
22‑Jun‑2009 | Netherlands F3 | Clay | R16 | 291 | 1178 | (1)Middelkoop d. (Q)Alexander Blom [AHO] | 6-1 6-2 | | | | | | | | | |
22‑Jun‑2009 | Netherlands F3 | Clay | R32 | 291 | 1191 | (1)Middelkoop d. (Q)Bas Van Der Valk [NED] | 6-4 4-6 6-4 | | | | | | | | | |
18‑May‑2009 | Cremona CH | Hard | R32 | 290 | 234 | (4)Marco Chiudinelli [SUI] d. Middelkoop | 6-1 6-2 | | | | | | | | | |
3‑May‑2009 | Munich | Clay | Q1 | 296 | 507 | Gero Kretschmer [GER] d. Middelkoop | 1-6 6-3 6-2 | | | | | | | | | |
20‑Apr‑2009 | Sofia CH | Clay | R32 | 304 | 96 | (1)Ivo Minar [CZE] d. (Q)Middelkoop | 6-4 6-4 | | | | | | | | | |
23‑Mar‑2009 | Barletta CH | Clay | R16 | 324 | 178 | Yuri Schukin [KAZ] d. (Q)Middelkoop | 5-7 6-3 7-5 | | | | | | | | | |
23‑Mar‑2009 | Barletta CH | Clay | R32 | 324 | 181 | (Q)Middelkoop d. Kristian Pless [DEN] | 1-0 RET | | | | | | | | | |
16‑Mar‑2009 | Caltanissetta CH | Clay | R32 | 266 | 429 | (Q)Francesco Aldi [ITA] d. Middelkoop | 6-1 6-3 | | | | | | | | | |
6‑Mar‑2009 | Davis Cup WG R1: ARG vs NED | Clay | RR | 268 | 50 | Martin Vassallo Arguello [ARG] d. Middelkoop | 6-2 6-4 | | | | | | | | | |
23‑Feb‑2009 | Delray Beach | Hard | Q1 | 269 | 207 | Peter Polansky [CAN] d. Middelkoop | 6-4 6-4 | | | | | | | | | |
16‑Feb‑2009 | Marseille | Hard | Q3 | 259 | 346 | Jerzy Janowicz [POL] d. Middelkoop | 6-4 6-2 | | | | | | | | | |
16‑Feb‑2009 | Marseille | Hard | Q2 | 259 | 202 | Middelkoop d. Sebastien De Chaunac [FRA] | 6-4 6-7(6) 6-3 | | | | | | | | | |
16‑Feb‑2009 | Marseille | Hard | Q1 | 259 | 490 | Middelkoop d. (WC)Julien Jeanpierre [FRA] | 7-5 6-2 | | | | | | | | | |
9‑Feb‑2009 | Rotterdam | Hard | Q1 | 256 | 55 | (1)Marc Gicquel [FRA] d. (WC)Middelkoop | 6-2 4-6 7-6(2) | | | | | | | | | |
2‑Feb‑2009 | Zagreb | Hard | Q1 | 257 | 425 | Ivan Dodig [CRO] d. Middelkoop | 6-3 7-6(8) | | | | | | | | | |
19‑Jan‑2009 | Australian Open | Hard | Q2 | 259 | 218 | Alexander Kudryavtsev [RUS] d. Middelkoop | 6-3 2-6 6-2 | | | | | | | | | |
19‑Jan‑2009 | Australian Open | Hard | Q1 | 259 | 95 | Middelkoop d. (1)Paul Capdeville [CHI] | 6-3 2-6 6-4 | | | | | | | | | |
12‑Jan‑2009 | Auckland | Hard | Q3 | 259 | 68 | (3)Bobby Reynolds [USA] d. Middelkoop | 6-4 6-2 | | | | | | | | | |
12‑Jan‑2009 | Auckland | Hard | Q2 | 259 | 76 | Middelkoop d. (6)Diego Junqueira [ARG] | 6-1 6-1 | | | | | | | | | |
12‑Jan‑2009 | Auckland | Hard | Q1 | 259 | 357 | Middelkoop d. Nathan Thompson [USA] | 7-6(6) 7-6(5) | | | | | | | | | |