Palestino were the defending champions, but were knocked out of the competition by Santiago Morning in the second round.
Unlike the previous edition, ties in this round were single-legged, with the team from the lower tier hosting the match.
[2] The 16 Primera División teams entered the competition at this stage, and were drawn against the 16 first round winners.
[6] Starting from this round, the order of legs in each tie will depend on the number assigned to each second round winner, with the team with the highest number in each tie hosting the second leg.
[7] With the ANFP's Council of Presidents voting to conclude the 2019 season on 29 November 2019, it was decided that both the semifinals and final would be single-legged series to be played in January 2020.