1. Runde
18.07.2009 MFK Mikolaiv - FK Olkom 3:0
NK Veres - Hirnyk-Sport 2:0
FK Bastion - FK Kremin 2:1
Irpen Horenychi - Dinamo Khmelnitskiy n.gesp.
FC Sumy - FK Bukovina 2:1
Shakhtar Sverdlovsk - FK Ros 1:0
Hirnyk Kryvyi Rih - Dnipro-75 3:1 i.E.
FK Morshyn - Olimpik Donetsk n.gesp.
2. Runde
04.08.2009 16:00 FK Bastion - Krymteplitsia Molodizhne 0:3
17:00 Energetik Burshtin - Helios Kharkiv 6:5 i.E.
05.08.2009 16:00 Yednist Pliski - Hirnyk Kryvyi Rih 5:1 n.V.
16:00 MFK Mikolaiv - Prykarpattya Ivano-Frankivsk 1:0
16:00 Irpen Horenychi - Volyn Lutsk 1:4
16:00 FK Poltava - FK Lviv 1:0
16:00 Shakhtar Sverdlovsk - FK Morshyn 2:0
16:00 Titan Armyansk - PFK Oleksandriya 0:2
16:30 Dnister Ovidiopol - Arsenal Bila Tserkva 1:0
17:00 Desna Chernigov - Niva Ternopil 1:2
17:00 PFK Niva Vinnytsia - FK Feniks-Illychovets Kalinine 0:1
17:00 Stal Alchevsk - PFK Sevastopol 2:1
17:00 NK Veres - CSKA Kiev 0:4
17:00 FC Sumy - Naftovik-Ukrnafta 0:1
17:00 Stal Dniprodzerzhynsk (old) - Zirka Kirovograd 1:0
3. Runde
15.08.2009 15:00 Stal Dniprodzerzhynsk (old) - Tavriya Simferopol (1958-2014) 0:4
15:00 FK Poltava - FK Feniks-Illychovets Kalinine 0:2
15:30 Shakhtar Sverdlovsk - FK Illichivets 1:3
16:00 Arsenal Kiev - Dinamo Kiev 1:2
16:00 Stal Alchevsk - Chernomorets Odessa 1:0
16:00 CSKA Kiev - FK Obolon Kiev 2:4 i.E.
16:00 Naftovik-Ukrnafta - Metalurh Donetsk 2:4 i.E.
16:00 Zakarpattya Uzhgorod - Dnipro Dnipropetrovsk 2:3
16:00 FK Kharkiv - Karpaty Lviv 1:5
16:00 Dnister Ovidiopol - Shakhtar Donetsk 1:6
16:00 MFK Mikolaiv - Krymteplitsia Molodizhne 0:1
16:00 Yednist Pliski - Niva Ternopil 2:1
16:00 Energetik Burshtin - Metalist Kharkiv 0:1
17:00 FK Krivbas (old) - Zorya Lugansk 5:0
17:00 PFK Oleksandriya - Volyn Lutsk 2:3 n.V.
18:00 Vorskla Poltava - Metalurg Zaporizhya 2:3 n.V.
Achtelfinale
12.09.2009 14:00 Yednist Pliski - Shakhtar Donetsk 1:3
15:00 FK Feniks-Illychovets Kalinine - Dnipro Dnipropetrovsk 1:2
15:00 Stal Alchevsk - FK Obolon Kiev 0:3
17:00 Volyn Lutsk - FK Krivbas (old) 2:1
17:00 Tavriya Simferopol (1958-2014) - FK Illichivets 4:2
17:00 Krymteplitsia Molodizhne - Metalurg Zaporizhya 1:2
17:00 Metalurh Donetsk - Karpaty Lviv 2:1
18:00 Metalist Kharkiv - Dinamo Kiev 0:1
Viertelfinale
28.10.2009 17:00 Volyn Lutsk - Metalurg Zaporizhya 2:1 n.V.
17:00 Tavriya Simferopol (1958-2014) - FK Obolon Kiev 4:0
18:00 Dnipro Dnipropetrovsk - Metalurh Donetsk 1:2 n.V.
18:30 Shakhtar Donetsk - Dinamo Kiev 2:0
Halbfinale
24.03.2010 17:00 Metalurh Donetsk - Shakhtar Donetsk 2:1
17:00 Volyn Lutsk - Tavriya Simferopol (1958-2014) 1:2
Finale
16.05.2010 16:00 Tavriya Simferopol (1958-2014) - Metalurh Donetsk 3:2 (2:0, 2:2) n.V.
Kubok
Kubok