Cristiano Ronaldo missed a late penalty on his record-breaking 128th Portugal appearance as Fernando Santos' team were head to a 0-0 draw by Group F rivals Austria at the Parc des Princes.
Ronaldo surpassed his country's cap milestone previously held by Luis Figo, who watching on from the stands, but failed to lead his side to a first victory at Euro 2016 as he hit the post with a spot-kick in the 79th minute before having a headed goal correctly disallowed for offside.
Nani also struck the woodwork with a header in the first half, but Ronaldo was the main culprit as Portugal somehow failed to score despite having 23 shots on goal throughout the 90 minutes.
The Real Madrid superstar won the penalty himself by being fouled by Martin Hinteregger, but missed the target despite sending Austria goalkeeper Robert Almer - who made a string of impressive saves earlier in the game - the wrong way.
4 - Cristiano Ronaldo has now failed to score four of his last five penalties for club & country (excl. shoot-outs). Blooper.-- OptaJohan (@OptaJohan) June 18, 2016
Portugal captain Ronaldo was teased by the chants of "Messi" from Austria's supporters throughout, and there was more agony for him as he had glancing header ruled out with five minutes remaining.
Santos' side sit third behind Iceland in Group F having scored fewer goals than the team Ronaldo infamously mocked after their meeting in Saint-Etienne, while Austria remain bottom despite picking up their first point at the tournament.
Martin Harnik was deployed as Austria's lone striker with Marcel Sabitzer replacing Marc Janko.
Within three minutes coach Marcel Koller may have been ruing the absence of Janko's aerial threat when Harnik peeled away from Pepe and headed a cross from Sabitzer wide from inside the six-yard box.
Portugal heeded the warning but Nani saw his attempt to guide the ball into the bottom-right corner diverted away by the leg of Almer, who remained alert to turn Vieirinha's dipping 25-yard strike around the post in the 13th minute.
Portugal remained in the ascendancy and Ronaldo missed a glorious chance to put them ahead following a neat one-two between Raphael Guerreiro and Nani, steering Borussia Dortmund's new left-back's delivery wide of the near post.
Austria's defence, and in particular Almer, looked nervy under pressure and the post saved them from going behind to a header from Nani with 29 minutes on the clock.
Santos' side almost paid for their profligacy four minutes before half-time but Vieirinha somehow managed to head a David Alaba free-kick off the line.
Just as they did the first, Austria started the second half brightly with Stefan Ilsanker forcing Portugal goalkeeper Rui Patricio into action with a powerful drive from 25 yards.
The theme of the opening period continued as Portugal again asserted their dominance, Almer keeping Ronaldo's venomous, low drive out of the bottom-right corner with a strong hand.
Ronaldo rose to connect with the subsequent corner from Ricardo Quaresma, but again he failed to find a route past the Austria goalkeeper.
Alaba had a largely ineffectual night and was replaced by Alessandro Schopf in 65th minute, though a tangle with Pepe in the first half may have left its mark on the midfielder.
Portugal were handed a lifeline when Hinteregger hauled down Ronaldo inside the box as he looked to latch onto a Guerreiro cross, but the captain failed to convert from the spot.
Ronaldo had a goal correctly ruled out in the closing stages as Austria held firm for a draw, with qualification from the group going down to the wire.