The 2005–06 Estonian Cup () was the 16th season of the Estonian football knockout tournament. Originally, winners of the cup qualified for the 2006–07 UEFA Cup first qualifying round. The defending champion, Levadia, was knocked out in the second round against later cup winners TVMK.
The competition culminated with the final held at Kadriorg Stadium, Tallinn on 17 May 2006 with TVMK taking the title 1–0. Since the TVMK also win the 2005 Meistriliiga, the runners-up Flora were qualified to the UEFA Cup.
All in all, 32 teams took part of the competition.
First round
!colspan="3" align="center"|31 August
!colspan="3" align="center"|1 September
!colspan="3" align="center"|6 September
!colspan="3" align="center"|7 September
Second round
!colspan="3" align="center"|9 November
!colspan="3" align="center"|10 November
Notes 1 Merkuur were renamed to Maag during the winter break. 2 Maag were merged with Warrior.
Quarter-finals
Semi-finals
Final
External links Official site
References Estonia Cup 2005/06 at RSSSF