The first round pairs were drawn by Estonian Football Association on 2 June 2010. A total of 96 teams registered for the competition, a new competition record.[1]
6' Jevgeni Grafski 10' (pen.)41'47' Andrus Mitt 12'35'Mark Švets 16'42' Dmitri Njatin 23' Andrei Timofejev 28' (o.g.) Heigo Plotnik 53'Maksim Smirnov 90' Jevgeni Ginzburg
Notes:1This match originally ended 2–4 in favor of Rakvere. Later, it was discovered that Võru had fielded an ineligible player during the match. Therefore, this match was awarded to Rakvere 0–4.
Third round
These matches occurred between 31 August and 7 October 2010.
The 8 winners from the previous round competed in this stage of the competition. However, before this round took place, Raasiku FC Joker withdrew from the competition, meaning that Flora moved on to the semifinals automatically.[2] These matches took place on 12 and 13 April 2011.