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Cristiano Ronaldo became the leading goal scorer in international football history despite missing a penalty in Portugal's win with the Republic of Ireland.
The new Manchester United signing saw an early penalty saved by teenage goalkeeper Gavin Bazunu before John Egan's header gave the Irish the lead in the World Cup qualifier.
Following a lengthy VAR delay, Bazunu dove to his right to save splendidly from the Portugal captain as Stephen Kenny's side defended valiantly in the Algarve.
The 36-year-old's late brace moved him clear of Ali Daei as the leading international goal scorer of all-time with a total of 111 goals for Portugal.
The hosts started dominantly and won a penalty after just 10 minutes after Jeff Hendrick fouled Bruno Fernandes in the area after stretching for the ball in the box.
However, after a five minute VAR check, Ronaldo was denied by a stunning save from Bazunu, who is on loan at League One Portsmouth from Manchester City.
Kenny's men rallied after the penalty miss and grew into the game after weathering the early storm, before taking the lead on the stroke of half-time.
It could even be argued that their goal came in line with the run of play as John Egan rose highest to head a Jamie McGrath header beyond Rui Patricio.
The goal was Egan's first for Ireland in his 15th cap and kickstarts their World Cup qualifying campaign after defeats in their opening two matches.
These included an embarrassing home loss to Luxembourg in March in their most recent competitive international fixture.
After the interval, Aaron Connolly went close to adding to the Irish lead as he was set up by Egan, but the Brighton forward saw his shot flash narrowly wide.
The Irish defence produced a dogged display against the 2016 European Champions as they produced 11 blocks as the Portuguese had 24 attempts on goal.
Portugal's continued pressure on the Irish goal was finally rewarded in the 89th minute as Ronaldo headed beyond the exceptional Bazunu.
Ireland almost grabbed a second moments later, though, as substitute James McLean forced a save from Patricio at the near post.
However, Ronaldo broke Irish hearts in the final minute of stoppage time with a second header at the back post to win the match and take his international tally to 111 goals.
Kenny's side will look to bounce back from the late heartbreak when they host Azerbaijan in their next match on Saturday at the Aviva Stadium.
- Cristiano Ronaldo
- World Cup
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