Manchester United and AC Milan needed 26 penalties to separate them in a shoot-out - with the Red Devils prevailing 9-8 after a 1-1 draw.
Alexis Sanchez's 12th-minute strike was cancelled out three minutes later as Manchester United beat the Italians in Carson, California.
The Chilean slotted a shot past Gianluigi Donnarumma to open the scoring in the International Champions Cup clash, but Suso drew the Serie A side level.
With the scores tied 1-1 after 90 minutes, United went on to win the penalty shootout 9-8 after 13 penalties each as Ander Herrera scored his second spot-kick while Franck Kessie sent his over the bar with an attempted Panenka.
Sadio Mane's stoppage-time penalty sealed a 2-1 comeback win for Liverpool over Manchester City in the International Champions Cup.
After a goalless first half to the match in New York, the game came to life in the second with Leroy Sane breaking the deadlock to put City ahead after 57 minutes.
Their lead did not last long, however, as Mohamed Salah buried a header six minutes later - with his second touch of the game and just 52 seconds after coming off the bench.
The Egyptian came close to scoring another two in the closing minutes - a header was blocked on the line and his second effort struck the crossbar.
But the period of concerted pressure from the Reds finally paid off in injury time.
Awarded a penalty when Dominic Solanke was fouled in the back by Tosin Adarabioyo, Liverpool forward Mane rolled his spot-kick to the left as Joe Hart dived in the opposite direction, providing a dramatic close to the match between the Premier League rivals.
Fernando Llorente and Lucas Moura each scored first-half doubles to lead Tottenham to a 4-1 win over Roma in the International Champions Cup.
The side, who were without their nine World Cup semi-finalists, put on a composed performance following a shaky start at the SDCCU Stadium in San Diego.
Patrik Schick had opened the scoring for Roma after just three minutes, firing into the far corner.
But a header from Llorente cancelled out their lead six minutes later, before the Spaniard swept in a rebound to complete his double and make it 2-1.
Moura added a brace of his own before half-time, heading in a cross from Serge Aurier and then scoring from the edge of the box a minute before the break.
The second half saw some fine chances for Roma, with Edin Dzeko's header from a corner going a couple of yards over before sub keeper Paulo Gazzaniga was equal to a late effort from the former Manchester City striker.
