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Cristiano Ronaldo's wait for his next trophy was prolonged on Tuesday night as Al-Nassr crashed out of the King's Cup.
The sporting icon, now 40, has not won a single competitive tournament in the Middle East since making the big money move from Manchester United in December 2022.
And Ronaldo's latest heartache came at the hands of his former team-mate Karim Benzema, who spearheaded Al-Ittihad to a win over Al-Nassr in the King's Cup round of 16 last night.
The Portuguese legend's men got off to the worst possible start when Benzema, who's bagged four goals so far this season, put the visitors ahead with a side-footed effort on 15 minutes.
But Al-Nassr rallied and found their way back into the game before the half-hour mark through Angelo Gabriel, who latched onto a Ronaldo cross before rifling an effort into the roof of the Al-Ittihad net.
The Riyadh-based club's joy was however short-lived as Hassem Aouar put Al-Ittihad in the lead before the break.
Cristiano Ronaldo 's wait for his next trophy was prolonged on Tuesday night as Al-Nassr crashed out of the King's Cup
Karim Benzema spearheaded Al-Ittihad to the victory of Ronaldo's men despite going down to 10-men
Despite being reduced to 10 men in the second half, it was ultimately a lead which Benzema, N'Golo Kante and co held onto in order to ensure their place in the King's Cup quarter-final.
The defeat comes as another woe for Ronaldo, who missed a number of good chances to score an equaliser during the second 45.
Arguably his biggest opportunity came moments after Al-Ittihad were reduced to 10. The former Juventus winger was baring down on goal but tried an audacious chip which was tame and easily gathered by the goalkeeper.
As is custom with Ronaldo, he also took control of his side's free-kicks. After missing two earlier in the game, the Portuguese was handed another chance to fire home from a set piece right at the death. His effort, from around 30 yards out, was however underwhelming and straight at the wall.
Despite their disappointing performance in the cup, Al-Nassr have enjoyed a promising start to their league campaign.
Managed by Jorge Jesus, they sit top of the Saudi Pro League after six games with 18 points. Ronaldo, who's now nearing 1000 professional goals, has netted seven goals and provided two assists.
With next summer's North American World Cup on the horizon, some had speculated that the tournament could offer Ronaldo the dream farewell to football if he leads Portugal to glory.
However the forward, who will be 41 when he boards the plane to the States, revealed earlier this month that he has no intention of hanging up his boots just yet.
Ronaldo has not won a single competitive tournament in the Middle East since making the big money move from Manchester United in December 2022
Speaking at the Portugal Football Globe Awards, he said: 'I want to keep playing for a few years, not many, I have to be honest.
'I want to thank all my team-mates for having learned from all of them - and even the younger generation as well. For me, it's a privilege to be with you.
'People, especially my family, say, "it's time for you to stop. You've done everything, why do you want to score 1,000 goals?" But I don't think so. I think I'm still producing good things, I'm helping my club and the national team and why not keep going?
'I'm sure that when it's over, I'll leave feeling fulfilled because I gave it my all. I know I don't have many more years but I try to enjoy the few I have to the fullest.'
