The 2008–09 Estonian Cup was the 19th season of the Estonian football knockout tournament. Winners of the cup qualified for the second qualifying round of the 2009–10 UEFA Europa League. The defending champions were Flora Tallinn, who successfully defended their title this year.
First round
!colspan="3" align="center"|22 July
!colspan="3" align="center"|23 July
!colspan="3" align="center"|30 July
!colspan="3" align="center"|6 August
The following teams received a bye in this round:
League Teams Meistriliiga Flora, TVMK, Narva Trans, Tulevik, Sillamäe Kalev Esiliiga Kuressaare, Lasnamäe Ajax, Warrior, Tamme Auto Second League Anži, Alko, Santos, Tabasalu PK, Sörve, Tarvastu, Ganvix, Warrior II Third League Saue, Piraaja, Lasnamäe Ajax Veteranid, Eurouniv, EBS Team, Ülikool Fauna, Metec, Noorus 96, Rada, Esteve, Kotkad, Atletik, Toompea, Püsivus, Haiba, Lelle, Vaprus III Fourth League HansaNet.ee, Enter, Soccernet, Quattromed, Otepää, Twister, Tribling, WC Guwalda, Kose, Dagöplast
Second round
!colspan="3" align="center"|5 August
!colspan="3" align="center"|6 August
!colspan="3" align="center"|7 August
!colspan="3" align="center"|12 August
!colspan="3" align="center"|13 August
!colspan="3" align="center"|14 August
!colspan="3" align="center"|19 August
!colspan="3" align="center"|20 August
!colspan="3" align="center"|21 August
!colspan="3" align="center"|27 August
Third round
!colspan="3" align="center"|2 September
!colspan="3" align="center"|3 September
!colspan="3" align="center"|4 September
!colspan="3" align="center"|6 September
!colspan="3" align="center"|9 September
!colspan="3" align="center"|11 September
!colspan="3" align="center"|17 September
Notes 1 Vaprus were disqualified from the competition because of the use of an ineligible player in their game against Ganvix.
Fourth round
!colspan="3" align="center"|23 September
!colspan="3" align="center"|24 September
!colspan="3" align="center"|1 October
!colspan="3" align="center"|8 October
!colspan="3" align="center"|11 October
!colspan="3" align="center"|26 October
Quarter-finals
Semi-finals
Final
FC FLORA TALLINN: GK 25 Mihkel AksaluRB 16 Markus Jürgenson CB 15 Tõnis VannaCB 24 Karl PalatuLB 19 Gert KamsCM 33 Aivar Anniste CM 5 Siksten KasimirRM 8 Oliver Konsa CM 6 Martin VunkLM 10 Henri AnierCF 9 Joonas Tamm Substitutes:GK 1 Stanislav PedõkDF 22 Mikk ReintamMF 2 Ken KallasteMF 7 Sergei Mošnikov MF 17 Henri RüütliFW 14 Vjatšeslav Zahovaiko FW 20 Alo Dupikov Manager: Tarmo RüütliJK NÕMME KALJU: GK 31 Rene KaasRB 7 Marcio Pimentel CB 2 Mikk Haavistu CB 25 Martin HurtLB 8 Alan ArrudaRM 9 Maksim Smirnov CM 28 Jevgeni Novikov CM 16 Murilo Maccari LM 18 Sergei Terehhov AM 5 Felipe NunesCF 19 Miroslav RõškevitšSubstitutes:GK 1 Daniil SavitskiDF 4 Risto KägoDF 12 Martin TšegodajevDF 24 Kristofer KaskMF 11 Tõnis Kaukvere MF 14 Janar Tükk FW 27 Anti KõluManager: Fredo Getulio
Top scorers
RankScorerClubGoals1 Felipe NunesNõmme Kalju102 Nikita AndreevLevadia9 Argo ArbeiterToompea94 Alar AlveLootos6 Deniss VassiljevKalju II6 Atko VäikmeriToompea67 Yaroslav DmitrievLevadia5 Kristjan TiirikTammeka / Narva Trans5 + 09 Jarmo AhjuperaFlora4 Irfan AmetovSillamäe Kalev4 Andreas AnikoKalju II4 Alo DupikovSillamäe Kalev / Flora4 + 0 Jaagup LuhakooderTulevik II4 Nikolai LõsanovNarva Trans4 Herkki OrroPaide4 Karlis SeirePaide4 Joonas TammTulevik II / Flora3 + 1 Ingemar TeeverNõmme Kalju4
External links Official site
References Estonia Cup 2008/09 at RSSSF