Cristiano Ronaldo suffered more Champions League misery as Juventus crashed out at the last-16 stage against 10-man Porto.

In the three years since he moved to Turin from Real Madrid, the Portugal superstar – a five-time Champions League winner – has yet to make it past the quarter-finals.

Here, the PA news agency looks back at Ronaldo's recent European agony.

2019: Juventus 1 Ajax 2 (agg 2-3) – quarter-finals

Ronaldo headed Juventus in front from a corner but that was as good as it got as Ajax's sensational run continued. Donny van de Beek controlled Hakim Ziyech's shot and slotted past Wojciech Szczesny to equalise and teenage captain Matthijs de Ligt's header secured their place in the semi-finals. Ronaldo's frustration was evident as he picked up a late yellow card for a lunge on Joel Veltman. It was his first defeat in the competition since Juventus beat Real in May 2015.

2020: Juventus 2 Lyon 1 (agg 2-2, Lyon won on away goals) – last 16

Ronaldo scored twice but it was not enough as Juventus were sent crashing out in the last 16 by Lyon. Leading 1-0 from February's first leg, the French side were handed a soft early penalty which Memphis Depay converted with a Panenka. That left Juve needing to score three to progress, and Ronaldo pulled one back from the penalty spot. He then fired home his 130th Champions League goal on the hour mark, but Lyon held on.

2021: Juventus 3 Porto 2 (agg 4-4, Porto won on away goals) – last 16

Sergio Oliveira's free-kick deep into extra time stunned Juve and sent Porto through on away goals. Oliveira's long-range strike, in the 115th minute, went through the legs of Ronaldo in the Juventus wall. Adrien Rabiot's thumping header two minutes later gave the Italian champions hope but the Portuguese side, who lost Mehdi Taremi to a 54th-minute red card, advanced on away goals.