Lionel Messi has experienced the highest of highs in the Champions League, winning the competition four times, but the lowest of lows too, suffering some heartbreaking defeats.
The Argentine has failed to get his hands on the trophy since lifting it with Barcelona in 2015, crashing out before the final every season since.
He hasn’t lifted the trophy since he was 27 years old and there’s every chance Barcelona’s treble triumph eight years ago will be the last time he lays his hands on ‘Ol Big Ears.
Each of the losses would have hurt, but which hurt the most? Well, because we’re a bit sadistic, we’ve gone ahead and ranked them all.
8. PSG 0 Bayern Munich 3 – 2023
PSG never came remotely close to winning this match-up, let alone the competition, but weren’t completely humiliated, and Messi could wipe away any tears with the World Cup winners’ medal he got a few months before. As painless as a Champions League exit can get.
"PSG were built to win the Champions League but they have been miles from it"
"The PSG project ultimately looks like its going to be a failure."
— Football on BT Sport (@btsportfootball) March 8, 2023
7. Barcelona 2 PSG 5 – 2021
They say it’s the hope that kills you, and there never really was much hope in this last 16 tie.
Barcelona, struggling under Ronald Koeman, headed into it as underdogs, and while Messi gave his side the lead in the first leg, Kylian Mbappe then got the chance to test the worst Barca backline in years, and that was that.
The Frenchman got a hat-trick in Catalonia and gave PSG the lead in the return leg, never giving Messi and an ailing Barca side a sniff of progression.
6. Juventus 3 Barcelona 0 – 2017
Messi and his team-mates may have believed a Champions League triumph was meant to be following their remarkable comeback against PSG in the previous round.
But Juventus never let them get too carried away with that thought, winning 3-0 in Turin before comfortably getting a goalless draw in Spain to progress to the semis.
5. PSG 2 Real Madrid 3 – 2022
A tie that was both classic PSG and classic Real Madrid.
Messi missed the last 16 first leg in Paris but his blushes were spared when a moment of Mbappe brilliance gave the Parisiens a 1-0 lead to take to the Bernabeu.
Mbappe then put PSG ahead in the Spanish capital, giving them a two-goal advantage going into the second half of the second leg. They’d been the better side throughout and appeared to be cruising to the quarter-finals.
Karim Benzema had other ideas, pouncing on an error from Gianluigi Donnarumma and going on to score a brilliant hat-trick in a madcap 17-minute period.
Madrid had turned the tie around in the blink of an eye – something they’d make a habit of doing all the way to lifting the trophy in PSG’s backyard.
4. Barcelona 2 Atletico Madrid 3 – 2016
Luis Enrique’s Barcelona looked absolutely unstoppable in 2015-16.
They’d won the treble the year before and would end up with a domestic double. They’d broken the back of their title charge with 12 successive league wins in the Spring and beaten La Liga rivals Atletico Madrid 2-1 in the first leg of the Champions League quarter-finals.
Messi, Suarez and Neymar were at the peak of their powers but they had no answer to Atleti in the second leg as Simeone’s side produced a defensive masterclass to shut them out at the Vicente Calderon.
Antoine Griezmann put them ahead on away goals midway through the first half and a late penalty sealed it.
3. Barcelona 2-8 Bayern Munich – 2020
This wasn’t even over two legs. A one-leg special during the Covid-inflicted 2019-20 campaign. The symbol of Barcelona’s fall from grace.
Just utterly brutal.
2. Barcelona 4 Roma 4 – 2018
Barcelona weren’t entirely convincing in the first leg of their 2018 quarter-final, but they were clinical and efficient to take a comfortable 4-1 lead back to the Italian capital.
Edin Dzeko’s late away goal at Camp Nou gave Roma a sniff, but nobody really expected them capable of overturning a three-goal deficit.
But they did. Kostas Manolas’ unforgettable header put Roma ahead on away goals and sent Barcelona into a tailspin.
Manolas’ goal vs Barcelona 🔥
Iconic Peter Drury commentary 🤩 pic.twitter.com/7pVFADSX6j
— Football Videos That Go Hard (@hardfootyvids) September 2, 2022
1. Barcelona 3 Liverpool 4 – 2019
Barcelona travelled to Merseyside for this semi-final with a first-leg 3-0 lead and painful memories of the Olimpico the year before. They had one foot in the final. It couldn’t happen again, could it?
“Come on, guys, let’s take a step forward,” Messi told his team-mates at half-time of the second leg at Anfield.
“We can’t pass up this opportunity. Give it your all, we’re there. We’re going to start [the second half] strong. Remember, what happened at Roma was our fault, no one else’s. Don’t let the same thing happen again. It was our fault and nothing more.”