30‑Nov‑2009 | Khanty-Mansiysk CH | Carpet | R16 | 274 | 390 | Jan Mertl [CZE] d. (3)Okun | 6-7(6) 7-6(3) 7-5 | | | | | | | | | |
30‑Nov‑2009 | Khanty-Mansiysk CH | Carpet | R32 | 274 | 579 | (3)Okun d. (Q)Mikhail Fufygin [RUS] | 6-7(2) 6-4 6-1 | | | | | | | | | |
23‑Nov‑2009 | Helsinki CH | Carpet | R32 | 254 | 264 | Tobias Kamke [GER] d. Okun | 6-4 1-0 RET | | | | | | | | | |
2‑Nov‑2009 | Astana CH | Hard | R16 | 265 | 117 | (3)Bjorn Phau [GER] d. Okun | 6-3 7-5 | | | | | | | | | |
2‑Nov‑2009 | Astana CH | Hard | R32 | 265 | 194 | Okun d. Ivan Sergeyev [UKR] | 6-3 6-2 | | | | | | | | | |
25‑Oct‑2009 | St. Petersburg Q | Hard | Q3 | 271 | 218 | (4)Yuri Schukin [KAZ] d. (6)Okun | 2-6 6-2 7-6(6) | | | | | | | | | |
25‑Oct‑2009 | St. Petersburg Q | Hard | Q2 | 271 | | (6)Okun d. (WC)Alexey Iremashvili [RUS] | 6-2 6-2 | | | | | | | | | |
25‑Oct‑2009 | St. Petersburg Q | Hard | Q1 | 271 | 879 | (6)Okun d. Vitali Reshetnikov [RUS] | 6-2 6-2 | | | | | | | | | |
19‑Oct‑2009 | Moscow Q | Hard | Q2 | 280 | 190 | (5)Illya Marchenko [UKR] d. Okun | 6-3 3-6 6-4 | | | | | | | | | |
19‑Oct‑2009 | Moscow Q | Hard | Q1 | 280 | | Okun d. (WC)Alexey Iremashvili [RUS] | 7-6(4) 6-4 | | | | | | | | | |
11‑Oct‑2009 | Shanghai Masters Q | Hard | Q2 | 294 | 79 | (5)Florian Mayer [GER] d. Okun | 6-3 6-4 | | | | | | | | | |
11‑Oct‑2009 | Shanghai Masters Q | Hard | Q1 | 294 | 117 | Okun d. (8)Brendan Evans [USA] | 4-6 7-6(2) 3-0 RET | | | | | | | | | |
7‑Sep‑2009 | Israel F6 | Hard | F | | 1071 | (1)Okun d. Marcus Daniell [NZL] | 7-6(4) 6-2 | | | | | | | | | |
7‑Sep‑2009 | Israel F6 | Hard | SF | | | (1)Okun d. (3)Pirmin Haenle [GER] | 6-1 6-2 | | | | | | | | | |
7‑Sep‑2009 | Israel F6 | Hard | QF | | | (1)Okun d. (7)Carl Bergman [SWE] | 6-3 6-4 | | | | | | | | | |
7‑Sep‑2009 | Israel F6 | Hard | R16 | | 1049 | (1)Okun d. John Paul Fruttero [USA] | 6-1 6-2 | | | | | | | | | |
7‑Sep‑2009 | Israel F6 | Hard | R32 | | 1427 | (1)Okun d. Noam Yitzhaki [ISR] | 6-3 6-0 | | | | | | | | | |
31‑Aug‑2009 | Israel F5 | Hard | F | 336 | 499 | (1)Okun d. (3)Miloslav Mecir [SVK] | 6-3 6-2 | | | | | | | | | |
31‑Aug‑2009 | Israel F5 | Hard | SF | 336 | 846 | (1)Okun d. (7)Patrik Rosenholm [SWE] | 6-2 6-0 | | | | | | | | | |
31‑Aug‑2009 | Israel F5 | Hard | QF | 336 | | (1)Okun d. (6)Gd Jones [NZL] | 6-2 6-3 | | | | | | | | | |
31‑Aug‑2009 | Israel F5 | Hard | R16 | 336 | 1307 | (1)Okun d. Andrei Vasilevski [BLR] | 6-4 6-1 | | | | | | | | | |
31‑Aug‑2009 | Israel F5 | Hard | R32 | 336 | 1700 | (1)Okun d. (WC)Gilad Ben Zvi [ISR] | 6-3 6-4 | | | | | | | | | |
24‑Aug‑2009 | Israel F4 | Hard | F | 329 | 886 | (1)Okun d. Mikal Oliver Statham [NZL] | 6-2 6-1 | | | | | | | | | |
24‑Aug‑2009 | Israel F4 | Hard | SF | 329 | 504 | (1)Okun d. (3)Ludovic Walter [FRA] | 6-2 6-3 | | | | | | | | | |
24‑Aug‑2009 | Israel F4 | Hard | QF | 329 | 1040 | (1)Okun d. John Paul Fruttero [USA] | 3-6 6-3 6-2 | | | | | | | | | |
24‑Aug‑2009 | Israel F4 | Hard | R16 | 329 | 1080 | (1)Okun d. Nick Cavaday [GBR] | 6-1 6-1 | | | | | | | | | |
24‑Aug‑2009 | Israel F4 | Hard | R32 | 329 | 1082 | (1)Okun d. Tomer Hodorov [ISR] | 6-1 6-1 | | | | | | | | | |
29‑Jun‑2009 | Winnetka CH | Hard | R16 | 309 | 221 | Scoville Jenkins [USA] d. Okun | 2-6 6-3 6-4 | | | | | | | | | |
29‑Jun‑2009 | Winnetka CH | Hard | R32 | 309 | 349 | Okun d. Lester Cook [USA] | 6-3 6-4 | | | | | | | | | |
18‑May‑2009 | Cremona CH | Hard | R32 | 319 | 602 | (WC)Daniele Bracciali [ITA] d. (Q)Okun | 4-6 6-3 6-3 | | | | | | | | | |
4‑May‑2009 | Ramat Hasharon CH | Hard | R32 | 333 | 59 | (1)Dudi Sela [ISR] d. (WC)Okun | 6-1 6-1 | | | | | | | | | |
27‑Apr‑2009 | Rhodes CH | Hard | R32 | 344 | 104 | (3)Kevin Kim [USA] d. (Q)Okun | 6-4 7-6(9) | | | | | | | | | |
13‑Apr‑2009 | Johannesburg CH | Hard | R32 | 338 | 342 | (WC)Raven Klaasen [RSA] d. (Q)Okun | 6-4 7-6(6) | | | | | | | | | |
23‑Mar‑2009 | Khorat CH | Hard | QF | 347 | 203 | Rajeev Ram [USA] d. Okun | 4-6 7-6(5) 6-4 | | | | | | | | | |
23‑Mar‑2009 | Khorat CH | Hard | R16 | 347 | 136 | Okun d. (4)Mathieu Montcourt [FRA] | 6-3 4-6 7-5 | | | | | | | | | |
23‑Mar‑2009 | Khorat CH | Hard | R32 | 347 | 498 | Okun d. (Q)Evgeny Donskoy [RUS] | 6-2 6-3 | | | | | | | | | |
16‑Mar‑2009 | Bangkok CH | Hard | SF | 393 | 158 | Danai Udomchoke [THA] d. (Q)Okun | 3-6 6-2 6-3 | | | | | | | | | |
16‑Mar‑2009 | Bangkok CH | Hard | QF | 393 | 86 | (Q)Okun d. (1)Andreas Beck [GER] | 6-4 6-2 | | | | | | | | | |
16‑Mar‑2009 | Bangkok CH | Hard | R16 | 393 | 317 | (Q)Okun d. (Q)Rohan Bopanna [IND] | 4-6 6-3 6-3 | | | | | | | | | |
16‑Mar‑2009 | Bangkok CH | Hard | R32 | 393 | 138 | (Q)Okun d. (6)Michail Elgin [RUS] | 7-6(7) 6-4 | | | | | | | | | |
2‑Feb‑2009 | Israel F3 | Hard | F | 434 | 265 | (1)Harel Levy [ISR] d. (3)Okun | W/O | | | | | | | | | |
2‑Feb‑2009 | Israel F3 | Hard | SF | 434 | 311 | (3)Okun d. (2)Attila Balazs [HUN] | 7-5 6-2 | | | | | | | | | |
2‑Feb‑2009 | Israel F3 | Hard | QF | 434 | 513 | (3)Okun d. (6)Igor Sijsling [NED] | 6-4 7-6(3) | | | | | | | | | |
2‑Feb‑2009 | Israel F3 | Hard | R16 | 434 | 799 | (3)Okun d. Patrik Rosenholm [SWE] | 6-1 6-0 | | | | | | | | | |
2‑Feb‑2009 | Israel F3 | Hard | R32 | 434 | 975 | (3)Okun d. Carl Bergman [SWE] | 6-2 6-4 | | | | | | | | | |
26‑Jan‑2009 | Israel F2 | Hard | F | | | (3)Okun d. (1)Harel Levy [ISR] | 6-4 6-4 | | | | | | | | | |
26‑Jan‑2009 | Israel F2 | Hard | SF | | | (3)Okun d. Mikhail Fufygin [RUS] | 6-4 6-4 | | | | | | | | | |
26‑Jan‑2009 | Israel F2 | Hard | QF | | | (3)Okun d. Filip Zeman [CZE] | 3-6 6-3 7-6(8) | | | | | | | | | |
26‑Jan‑2009 | Israel F2 | Hard | R16 | | | (3)Okun d. Patrik Rosenholm [SWE] | 6-2 6-2 | | | | | | | | | |
26‑Jan‑2009 | Israel F2 | Hard | R32 | | | (3)Okun d. Ismar Gorcic [BIH] | 3-6 6-1 6-4 | | | | | | | | | |