1. Round
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 dnp
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 aet
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. Round
04/08/2008 15:00 Olimpik Donetsk - Zirka Kirovograd 0:4
06/08/2008 15:00 Yednist Pliski II - Dnister Ovidiopol 2:4
15:00 Arsenal Bila Tserkva - Desna Chernigov 1:3
15:00 CSKA Kiev - FK Poltava 2:1 aet
15:00 FK Kremin - FK Komunalnyk Luhansk 2:4 pso
15:00 PFK Sevastopol - FK Feniks-Illychovets Kalinine 1:2 aet
15:00 FK Bastion - PFK Niva Vinnytsia 2:3 aet
15:00 Stal Dniprodzerzhynsk (old) - PFK Oleksandriya 0:2
15:30 FK Korosten - Knyazha Shchaslive 1:3
15:30 FK Olkom - Yednist Pliski 4:0
16:00 FK Podillya-Khmelnitskiy - Helios Kharkiv 1:2 aet
16:00 FK Obolon - Naftovik-Ukrnafta 3:1
16:00 FK Dnipro Cherkasy - Stal Alchevsk 2:3 aet
16:00 Zakarpattya Uzhgorod - Volyn Lutsk 4:2
16:00 Energetik Burshtin - Ihroservice Simferopol 0:1
16:00 Spartak Ivano-Frankivsk - Krymteplitsia Molodizhne 0:3
3. Round
12/09/2008 15:00 FK Illichivets - Shakhtar Donetsk 0:3
13/09/2008 12:00 FK Feniks-Illychovets Kalinine - FK Krivbas (old) 2:1
13:30 Helios Kharkiv - Zakarpattya Uzhgorod 0:1
14:00 Knyazha Shchaslive - FK Lviv 0:2
14:00 Dnister Ovidiopol - Metalist Kharkiv 1:4
14:00 CSKA Kiev - Tavriya Simferopol (1958-2014) 0:3
14:00 FK Komunalnyk Luhansk - Arsenal Kiev 0:3
14:00 Zirka Kirovograd - Vorskla Poltava 0:1
15:00 FK Olkom - Dinamo Kiev 0:5
16:00 Metalurg Zaporizhya - Metalurh Donetsk 2:3
16:00 Krymteplitsia Molodizhne - Dnipro Dnipropetrovsk 1:3
18:00 Desna Chernigov - FK Kharkiv 1:4
14/09/2008 14:00 PFK Niva Vinnytsia - Stal Alchevsk 1:4
14:00 PFK Oleksandriya - Karpaty Lviv 1:0
14:00 FK Obolon - Chernomorets Odessa 1:0
14:00 Ihroservice Simferopol - Zorya Lugansk 0:2
Round of 16
28/10/2008 12:00 FK Obolon - Vorskla Poltava 1:4
29/10/2008 10:00 FK Feniks-Illychovets Kalinine - Tavriya Simferopol (1958-2014) 0:2
12:00 Zakarpattya Uzhgorod - Shakhtar Donetsk 1:4
15:00 PFK Oleksandriya - Dnipro Dnipropetrovsk 6:5 pso
15:00 Stal Alchevsk - FK Lviv 2:0
16:00 FK Kharkiv - Metalurh Donetsk 0:2
17:00 Dinamo Kiev - Zorya Lugansk 2:0
17:00 Metalist Kharkiv - Arsenal Kiev 3:1
Quarter-finals
11/11/2008 15:00 PFK Oleksandriya - Shakhtar Donetsk 1:2
12/11/2008 15:00 Stal Alchevsk - Dinamo Kiev 1:4
15:00 Tavriya Simferopol (1958-2014) - Metalist Kharkiv 1:2
16:00 Metalurh Donetsk - Vorskla Poltava 0:1
Semi-finals
22/04/2009 16:00 Metalist Kharkiv - Vorskla Poltava 0:0
13/05/2009 17:45 Shakhtar Donetsk - Dinamo Kiev 1:0
16:00 Vorskla Poltava - Metalist Kharkiv 2:0
Final
31/05/2009 16:00 Vorskla Poltava - Shakhtar Donetsk 1:0 (0:0)
Kubok
Kubok