The 2026–27 Estonian Cup is the 37th season of the main domestic football knockout tournament in Estonia. The winners qualify for the 2027–28 UEFA Conference League first qualifying round. Flora were the defending cup holders.
First round 22 clubs entered the first round. The draw was held on 19 May 2026, alongside the Round of 64 draw.
!colspan="3" align="center"|10 June 2026
!colspan="3" align="center"|16 June 2026
!colspan="3" align="center"|18 June 2026
!colspan="3" align="center"|30 June 2026
!colspan="3" align="center"|2 July 2026
!colspan="3" align="center"|10 July 2026
Round of 64 45 clubs entered the Round of 64 alongside the 11 first round winners; the top four teams of the 2025 Meistriliiga (Flora, FCI Levadia, Nõmme Kalju, and Paide Linnameeskond) received byes. The draw was held on 19 May 2026, alongside the first round draw.
!colspan="3" align="center"|21 July 2026
!colspan="3" align="center"|22 July 2026
!colspan="3" align="center"|23 July 2026
!colspan="3" align="center"|24 July 2026
!colspan="3" align="center"|25 July 2026
!colspan="3" align="center"|26 July 2026
!colspan="3" align="center"|28 July 2026
!colspan="3" align="center"|29 July 2026
!colspan="3" align="center"|5 August 2026
Round of 32 The 28 Round of 64 winners and 4 teams given byes entered the Round of 32. The draw was held on 24 July 2026
!colspan="3" align="center"|5 August 2026
!colspan="3" align="center"|11 August 2026
!colspan="3" align="center"|12 August 2026
!colspan="3" align="center"|19 August 2026
!colspan="3" align="center"|26 August 2026
!colspan="3" align="center"|22 September 2026
!colspan="3" align="center"|22 October 2026
Round of 16 The 16 Round of 32 winners entered the Round of 16. The draw was held on 17 August 2026
!colspan="3" align="center"|26 August 2026
!colspan="3" align="center"|2 September 2026
!colspan="3" align="center"|24 September 2026
!colspan="3" align="center"|2 October 2026
!colspan="3" align="center"|3 October 2026
!colspan="3" align="center"|7 October 2026
!colspan="3" align="center"|TBD
References
External links Official website Estonian Cup on Soccerway.com