3‑Nov‑2008 | Great Britain F18 | Hard | R16 | 562 | 1392 | (Q)Milos Sekulic [SWE] d. (5)Skupski | 7-6(4) 4-6 6-3 | | | | | | | | | |
3‑Nov‑2008 | Great Britain F18 | Hard | R32 | 562 | 841 | (5)Skupski d. Daniel Cox [GBR] | 6-7(4) 6-4 6-4 | | | | | | | | | |
27‑Oct‑2008 | Great Britain F17 | Hard | R32 | 582 | 859 | (WC)Colin Fleming [GBR] d. (8)Skupski | 6-3 6-2 | | | | | | | | | |
20‑Oct‑2008 | Great Britain F16 | Hard | SF | 575 | 558 | (8)Daniel Evans [GBR] d. Skupski | 6-3 6-7(5) 6-3 | | | | | | | | | |
20‑Oct‑2008 | Great Britain F16 | Hard | QF | 575 | 621 | Skupski d. Bastian Knittel [GER] | 6-4 6-4 | | | | | | | | | |
20‑Oct‑2008 | Great Britain F16 | Hard | R16 | 575 | 559 | Skupski d. (7)Stefano Ianni [ITA] | 7-6(6) 7-5 | | | | | | | | | |
20‑Oct‑2008 | Great Britain F16 | Hard | R32 | 575 | 859 | Skupski d. (Q)Javier Marti [ESP] | 6-3 6-1 | | | | | | | | | |
15‑Sep‑2008 | Great Britain F15 | Hard | QF | 556 | | (1)Josh Goodall [GBR] d. (7)Skupski | 7-5 6-7(5) 6-2 | | | | | | | | | |
15‑Sep‑2008 | Great Britain F15 | Hard | R16 | 556 | 942 | (7)Skupski d. Joshua Milton [GBR] | 6-1 6-3 | | | | | | | | | |
15‑Sep‑2008 | Great Britain F15 | Hard | R32 | 556 | 1185 | (7)Skupski d. (Q)Maniel Bains [GBR] | 6-2 6-4 | | | | | | | | | |
8‑Sep‑2008 | Great Britain F14 | Hard | R16 | 551 | 1104 | (WC)Daniel Smethurst [GBR] d. (6)Skupski | 2-6 6-3 6-3 | | | | | | | | | |
8‑Sep‑2008 | Great Britain F14 | Hard | R32 | 551 | 1280 | (6)Skupski d. (Q)Kyle Brassington [GBR] | 6-4 6-4 | | | | | | | | | |
14‑Jul‑2008 | Manchester CH | Grass | R32 | 543 | 315 | Alexander Slabinsky [GBR] d. (WC)Skupski | 7-6(5) 7-5 | | | | | | | | | |
23‑Jun‑2008 | Wimbledon Q | Grass | Q1 | 527 | 289 | Noam Okun [ISR] d. (WC)Skupski | 6-4 6-2 | | | | | | | | | |
26‑May‑2008 | Kuwait F2 | Hard | R16 | 551 | 429 | (4)Brydan Klein [AUS] d. (Q)Skupski | 6-3 6-4 | | | | | | | | | |
26‑May‑2008 | Kuwait F2 | Hard | R32 | 551 | 1810 | (Q)Skupski d. (LL)Stefano Vukov [CRO] | 6-0 6-1 | | | | | | | | | |
19‑May‑2008 | Kuwait F1 | Hard | QF | 631 | 431 | (3)Brydan Klein [AUS] d. (7)Skupski | 6-4 6-2 | | | | | | | | | |
19‑May‑2008 | Kuwait F1 | Hard | R16 | 631 | 1839 | (7)Skupski d. (Q)Stefano Vukov [CRO] | 6-1 3-1 RET | | | | | | | | | |
19‑May‑2008 | Kuwait F1 | Hard | R32 | 631 | 1043 | (7)Skupski d. Dayne Kelly [AUS] | 6-1 6-0 | | | | | | | | | |
12‑May‑2008 | Greece F2 | Carpet | F | 630 | 1135 | (1)Skupski d. David Canudas Fernandez [ESP] | 6-3 6-3 | | | | | | | | | |
12‑May‑2008 | Greece F2 | Carpet | SF | 630 | 654 | (1)Skupski d. (3)Karlis Lejnieks [LAT] | 6-3 6-3 | | | | | | | | | |
12‑May‑2008 | Greece F2 | Carpet | QF | 630 | 1065 | (1)Skupski d. Daniel Danilovic [SWE] | 4-6 6-3 7-6(2) | | | | | | | | | |
12‑May‑2008 | Greece F2 | Carpet | R16 | 630 | | (1)Skupski d. (WC)Konstantinos Mikos [GRE] | 6-7(6) 6-0 6-2 | | | | | | | | | |
12‑May‑2008 | Greece F2 | Carpet | R32 | 630 | 1660 | (1)Skupski d. (Q)Konstantinos Kalaitzis [GRE] | 6-2 6-2 | | | | | | | | | |
5‑May‑2008 | Great Britain F8 | Clay | R32 | 630 | 376 | (1)Richard Bloomfield [GBR] d. Skupski | 6-2 6-0 | | | | | | | | | |
28‑Apr‑2008 | Great Britain F7 | Clay | R32 | 635 | 500 | (8)Ludovic Walter [FRA] d. Skupski | 6-1 6-0 | | | | | | | | | |
31‑Mar‑2008 | Great Britain F6 | Carpet | QF | | | (3)Conor Niland [IRL] d. Skupski | 7-5 7-5 | | | | | | | | | |
31‑Mar‑2008 | Great Britain F6 | Carpet | R16 | | | Skupski d. Rudy Coco [FRA] | 6-7(9) 7-6(6) 6-3 | | | | | | | | | |
31‑Mar‑2008 | Great Britain F6 | Carpet | R32 | | | Skupski d. (8)Juho Paukku [FIN] | 6-7(4) 7-6(5) 7-6(5) | | | | | | | | | |
24‑Mar‑2008 | Great Britain F5 | Hard | R32 | 665 | 306 | (3)Frederik Nielsen [DEN] d. Skupski | 6-2 6-3 | | | | | | | | | |
17‑Mar‑2008 | Great Britain F4 | Hard | QF | | | (1)Richard Bloomfield [GBR] d. Skupski | 7-6(1) 6-4 | | | | | | | | | |
17‑Mar‑2008 | Great Britain F4 | Hard | R16 | | | Skupski d. (5)Miles Kasiri [GBR] | 7-6(5) 6-0 | | | | | | | | | |
17‑Mar‑2008 | Great Britain F4 | Hard | R32 | | 1274 | Skupski d. (WC)Daniel Evans [GBR] | 6-4 6-4 | | | | | | | | | |
28‑Jan‑2008 | Great Britain F3 | Hard | SF | 705 | 668 | (8)Gregoire Burquier [FRA] d. Skupski | 7-6(3) 6-4 | | | | | | | | | |
28‑Jan‑2008 | Great Britain F3 | Hard | QF | 705 | 1180 | Skupski d. (Q)Matthew Illingworth [GBR] | 6-4 1-6 6-3 | | | | | | | | | |
28‑Jan‑2008 | Great Britain F3 | Hard | R16 | 705 | 955 | Skupski d. (Q)Henrik Norfeldt [SWE] | 6-4 3-6 6-3 | | | | | | | | | |
28‑Jan‑2008 | Great Britain F3 | Hard | R32 | 705 | 430 | Skupski d. (1)Nicolas Tourte [FRA] | 6-4 7-6(4) | | | | | | | | | |
21‑Jan‑2008 | Great Britain F2 | Hard | R32 | | | (Q)Wojciech Starakiewicz [POL] d. Skupski | 6-1 6-7(5) 7-6(8) | | | | | | | | | |
14‑Jan‑2008 | Great Britain F1 | Hard | R32 | 707 | 514 | (6)Miles Kasiri [GBR] d. Skupski | 6-7(4) 6-4 7-6(1) | | | | | | | | | |