MIAMI, Florida – The 2023 Leagues Cup Round of 16 finished up on Tuesday with five matches determining the quarterfinal match-ups.

After being suspended due to weather on Monday night, the Philadelphia Union secured their quarterfinal place by defeating the New York Red Bulls 4-3 in a penalty shootout following a 1-1 draw at Subaru Park in Chester, Pennsylvania. Nathan Harriel’s second half equalizer set the stage for the Union’s victory in spot kicks.

Nashville SC staged an instant classic with seven-time Concacaf champions Club America, taking a 6-5 penalty shootout win after a dramatic 2-2 draw between the two teams at GEODIS Park in Nashville, Tennessee.

Las Aguilas looked poised to win 2-1 on a Julian Quinones penalty conversion in the fourth minute of second half stoppage time, but Nashville got a last-gasp 2-2 equalizer through Sam Surridge to force the penalty shootout. From the spot, Nashville proved superior to earn their quarterfinal place.

A penalty shootout was also required to determine who would advance from the Minnesota United-Toluca affair at Allianz Field in Saint Paul, Minnesota. The home side raced out to a 2-0 lead, only to see Toluca rally for two goals in the second half. However, in the shootout, Minnesota United had the upper hand, winning 4-2.

City rivals Monterrey and Tigres squared off at Shell Energy Stadium in Houston, Texas and it ended with a late 1-0 victory for Monterrey. New arrival Sergio Canales converted a penalty deep into second half stoppage time to secure the dramatic victory for Rayados.

An all-MLS affair capped the night’s action with Los Angeles FC downing Real Salt Lake 4-0 at BMO Stadium in Los Angeles. Denis Bouanga scored a pair of goals to pave the way for a four-goal second half for LAFC.

All four quarterfinal matches will take place on Friday. The Philadelphia Union will host Queretaro, Inter Miami welcome in Charlotte FC, Nashville SC will face Minnesota United in Nashville and LAFC will meet Monterrey at the Rose Bowl in Pasadena, California.