Austria struck twice late on to ensure North Macedonia's debut at a major tournament ended in a spirited 3-1 defeat in Romania.
Igor Angelovski's side broke new ground by qualifying for Euro 2020 after a play-off win over Georgia last November.
And, having gone behind to Stefan Lainer's impressive finish, North Macedonia equalised in the first half when 37-year-old striker Goran Pandev became the European Championship's second oldest goalscorer.
But, like they did twice in qualifying, they came unstuck against the Austrians, who secured their maiden win at a Euros thanks to efforts from second-half substitutes Michael Gregoritsch and Marko Arnautovic.
Lainer netted in his country's 2-1 triumph over North Macedonia last November and needed just 18 minutes to haunt them again courtesy of a fine finish.
The right-back ghosted in at the back post and, having timed his run to perfection, volleyed home Marcel Sabitzer's drilled angled cross.
Austria almost doubled their advantage soon after, but the unmarked Sasa Kalajdzic stabbed Sabitzer's cross straight at Stole Dimitrievski.
But, just as Franco Foda's side looked set to dominate, North Macedonia hit back in the 27th minute through star man Pandev, who had struck the play-off winner against Georgia.
The former Inter Milan player registered another important goal for his country, his 38th, by tapping into an empty net after goalkeeper Daniel Bachmann raced out and failed to gather following a defensive mix-up.
Aleksandar Trajkovski looked fortunate to receive only a yellow card after appearing to elbow Aleksandar Dragovic in an aerial challenge.
Bachmann made amends for his earlier error by diving at the feet of Boban Nikolov to deny the wing-back after Eljif Elmas' exquisite pass carved the Austria defence open.
Dimitrievski then came to his side's rescue at the other end, diving full stretch to keep out Gregoritsch's smart header.
But the striker was not to be denied 12 minutes from time, nipping in ahead of Dimitrievski to prod home David Alaba's pinpoint cross.
Austria sensed blood and attempted to kill off the game, with Sabitzer having a shot blocked before they struck again at the death.
Former West Ham forward Arnautovic got in behind the North Macedonia defence and went past Dimitrievski before rolling the ball into the net