Flora won their eight title after defeating Narva Trans in the final.
The winner of the Cup were to qualify for the first qualifying round of the 2020–21 UEFA Europa League, but as Flora were already qualified for the Champions League the spot passed on to Paide Linnameeskond.
The draw was made by Estonian Football Association on 25 May 2019.
[4] The draw for the fourth round was made on 11 September 2019.
[5] The draw for the fourth round was made on 29 February 2020.