1. Runde
16.07.2008 NK Veres - FK Korosten 0:1
Yednist Pliski II - Hirnyk-Sport 3:0
Arsenal Bila Tserkva - Shakhtar Sverdlovsk 3:1
FK Poltava - Arsenal Kharkiv 4:1
FK Kremin - FK Bukovina n.gesp.
FK Podillya-Khmelnitskiy - FK Nafkom 4:0
FK Olkom - Dnipro-75 2:0
Titan Donetsk - Yednist Pliski 0:1
PFK Niva Vinnytsia - Titan Armyansk 3:1 n.V.
Stal Dniprodzerzhynsk (old) - Niva Ternopil 2:0
FK Ros - FK Bastion 1:3
Zirka Kirovograd - FK Yavir 1:0
Olimpik Donetsk - Hirnyk Kryvyi Rih 4:1
2. Runde
04.08.2008 16:00 Olimpik Donetsk - Zirka Kirovograd 0:4
06.08.2008 16:00 Yednist Pliski II - Dnister Ovidiopol 2:4
16:00 Arsenal Bila Tserkva - Desna Chernigov 1:3
16:00 CSKA Kiev - FK Poltava 2:1 n.V.
16:00 FK Kremin - FK Komunalnyk Luhansk 2:4 i.E.
16:00 PFK Sevastopol - FK Feniks-Illychovets Kalinine 1:2 n.V.
16:00 FK Bastion - PFK Niva Vinnytsia 2:3 n.V.
16:00 Stal Dniprodzerzhynsk (old) - PFK Oleksandriya 0:2
16:30 FK Korosten - Knyazha Shchaslive 1:3
16:30 FK Olkom - Yednist Pliski 4:0
17:00 FK Podillya-Khmelnitskiy - Helios Kharkiv 1:2 n.V.
17:00 FK Obolon - Naftovik-Ukrnafta 3:1
17:00 FK Dnipro Cherkasy - Stal Alchevsk 2:3 n.V.
17:00 Zakarpattya Uzhgorod - Volyn Lutsk 4:2
17:00 Energetik Burshtin - Ihroservice Simferopol 0:1
17:00 Spartak Ivano-Frankivsk - Krymteplitsia Molodizhne 0:3
3. Runde
12.09.2008 16:00 FK Illichivets - Shakhtar Donetsk 0:3
13.09.2008 13:00 FK Feniks-Illychovets Kalinine - FK Krivbas (old) 2:1
14:30 Helios Kharkiv - Zakarpattya Uzhgorod 0:1
15:00 Knyazha Shchaslive - FK Lviv 0:2
15:00 Dnister Ovidiopol - Metalist Kharkiv 1:4
15:00 CSKA Kiev - Tavriya Simferopol (1958-2014) 0:3
15:00 FK Komunalnyk Luhansk - Arsenal Kiev 0:3
15:00 Zirka Kirovograd - Vorskla Poltava 0:1
16:00 FK Olkom - Dinamo Kiev 0:5
17:00 Metalurg Zaporizhya - Metalurh Donetsk 2:3
17:00 Krymteplitsia Molodizhne - Dnipro Dnipropetrovsk 1:3
19:00 Desna Chernigov - FK Kharkiv 1:4
14.09.2008 15:00 PFK Niva Vinnytsia - Stal Alchevsk 1:4
15:00 PFK Oleksandriya - Karpaty Lviv 1:0
15:00 FK Obolon - Chernomorets Odessa 1:0
15:00 Ihroservice Simferopol - Zorya Lugansk 0:2
Achtelfinale
28.10.2008 13:00 FK Obolon - Vorskla Poltava 1:4
29.10.2008 11:00 FK Feniks-Illychovets Kalinine - Tavriya Simferopol (1958-2014) 0:2
13:00 Zakarpattya Uzhgorod - Shakhtar Donetsk 1:4
16:00 PFK Oleksandriya - Dnipro Dnipropetrovsk 6:5 i.E.
16:00 Stal Alchevsk - FK Lviv 2:0
17:00 FK Kharkiv - Metalurh Donetsk 0:2
18:00 Dinamo Kiev - Zorya Lugansk 2:0
18:00 Metalist Kharkiv - Arsenal Kiev 3:1
Viertelfinale
11.11.2008 16:00 PFK Oleksandriya - Shakhtar Donetsk 1:2
12.11.2008 16:00 Stal Alchevsk - Dinamo Kiev 1:4
16:00 Tavriya Simferopol (1958-2014) - Metalist Kharkiv 1:2
17:00 Metalurh Donetsk - Vorskla Poltava 0:1
Halbfinale
22.04.2009 17:00 Metalist Kharkiv - Vorskla Poltava 0:0
13.05.2009 18:45 Shakhtar Donetsk - Dinamo Kiev 1:0
17:00 Vorskla Poltava - Metalist Kharkiv 2:0
Finale
31.05.2009 17:00 Vorskla Poltava - Shakhtar Donetsk 1:0 (0:0)
Kubok
Kubok