Despite the two-week break in action, Head Coach Ronny Deila was able to name an unchanged lineup from the one which defeated Chicago in a wild 4-3 Decision Day victory.
That meant a midfield trio of Maxi Moralez, Keaton Parks and Alex Ring backed up the in-form attacking trio of Taty Castellanos, Gary Mackay-Steven and Jesus Medina as City looked to reach the Eastern Conference semifinals in our fifth consecutive MLS Playoffs appearance.
Standing in the way of a spot in the last four was a familiar foe in the shape of Orlando City, who had qualified for the postseason for the first time ever, finishing one position above NYCFC in fourth place in the standings.
City were coming in hot off four successive wins to end the regular season but they found themselves behind inside 5' after a penalty was awarded for a handball by Anton Tinnerholm. Nani assumed responsibility for the spot-kick and beat Sean Johnson to have the hosts up 1-0 early.
However, that lead lasted only three minutes as Maxime Chanot rose highest on a Jesus Medina corner and headed in to make it 1-1.
From there, Ronny's side dominated the opening half and would have taken an advantage in at the interval if not for some unbelievable goalkeeping from Orlando's Peruvian shot-stopper.
Pedro Gallese made a string of great saves in the first half but his best was on 43' when he produced an incredible double save to deny Taty Castellanos first, before he threw out a hand at Keaton Parks' rebound for an even better stop.
Despite the level scoreline, Deila will have been the happier of the two coaches at the break and his side continued to dominate after halftime, with Gallese again called to be at his best with another save, this time from Medina.
At the other end, Sean Johnson made a big save from a deflected Nani shot to keep his side level, but the half hinged on Orlando being reduced to ten men as the match entered stoppage-time after Ruan kicked out at Mackay-Steven for the red card.
With ten minutes to additional time added, Deila made three changes bringing in Nicolas Acevedo, Sebastien Ibeagha and Ismael Tajouri-Shradi but it was Orlando who nearly stole it in the last second of normal time, but Tesho Akindele's shot from six yards went just wide, much to the relief of the Boys in Blue.
In extratime, City couldn't find a way through so the match went to penalties where there was further drama in store, to put it mildly.
After Maxi Moralez missed the opening penalty, the following six were converted and for a moment it appeared as though Gallese's save from Castellanos with City's fifth and final PK had sent Orlando through.
After a VAR review, it was uncovered that the goalkeeper had come off his line and so he received a yellow card as a result - his second of the match - meaning he was shown a red card and NYC would be allowed a retake.
Backup GK Brian Rowe had taken his position in goal as a substitute but the referee then told him to go back to the sidelines as the rules dictate that a substitute can't be made during a shootout. Eventually, outfielder Rodrigo Schegel took up the spot and was unable to save Taty's second penalty.
Sean Johnson then saved Nani's penalty to take it to sudden death penalties where Gudi Thórarinsson was the unfortunate player to see his kick saved, allowing Orlando to advance to the Conference semifinals.
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