Palestino were faithful to the playing style imposed by Ecuadorian coach Octavio Zambrano, who prioritises speed and width.
Two of the match's first clear chances at goal came down the flanks, but striker German Ezequiel Cano could not open the scoring after seeing his first effort saved and his second come back off the crossbar.
His profligacy in front of goal was soon forgotten, as Luis Jimenez capitalised on passive Medellin defending to break the deadlock in the 41st minute, thanks in large part to a fortunate ricochet off goalkeeper David Gonzalez.
The Colombians were soon back on level terms before the half time break, after Palestino goalkeeper failed to keep out Luis David Murrillo's close-range header from a measured cross from the byline.
In the second half, both teams went all out for the goal that would tilt the round in their favour.
With both sides pouring men forward, spaces began to open up all over the pitch, but neither team could capitalise and convert any of their chances.
Despite the numerous chances to score, both goalkeepers and defences came out on top to send the match to penalties.
With the home crowd behind them, Cristobal Jorquera, Luis Mago, and Luis Jimenez scored in the penalty shootout for Palestino, while Diego Herazo and Andres Ricaurte missed for Medellin, with Elvis Perlaza the only one to convert a penalty kick for the visiting Colombian team.