With the scores finishing level at 1-1 after extra-time in Saturday's MLS playoff encounter, penalties were required to settle the contest.
NYCFC's Maxi Moralez stepped up to take the first penalty, hitting the crossbar, and 10-man Orlando stayed perfect to claim a 4-3 lead.
Valentin Castellanos took NYCFC's vital fifth penalty yet was denied by Pedro Gallese, who lunged low to his right, sparking Orlando celebrations.
However, a VAR check deemed that Gallese had moved off his line before the spot-kick had been taken and, to add further insult, Orlando's goalkeeper – who had earlier been booked for time-wasting – was shown a second yellow card.
Perplexed Lions coach Oscar Pareja had to be brought back onto the touchline, where he instructed substitute goalkeeper Brian Rowe to come on, despite having made five changes prior to the shootout.
Referee Allen Chapman allowed Rowe on, only to then be informed of his mistake and, after extensive discussions with his fellow officials, tell the goalkeeper to leave the pitch.
Defender Rodrigo Schlegel donned the gloves instead and could not get close to Castellanos' second attempt, with NYCFC's Sean Johnson then making an acrobatic stop to deny Nani and force sudden death.
Nicolas Acevedo and Robin Jansson exchanged successful spot-kicks, but Schlegel secured a place in MLS folklore when he saved Gudmundur Thorarinsson's effort.
There was still time for more drama, however, as referee Chapman signalled for full time, despite Orlando still having one more penalty to make. The league's official Twitter account also declared the Lions winners.
Orlando's players were celebrating once more before the official realised his error, but his blushes were spared when Benji Michel emphatically made sure of a 6-5 shootout triumph, capping an extraordinary series of events.