His illustrious career has endured heartbreak. Here are the most unforgettable ones.

Today, Lionel Messi turns 30. This sadly means one of the greatest footballers of all times draws ever closer to the end of his illustrious career.

And what an illustrious career it has been. The Argentine has won 30 trophies and numerous individual accolades, and does not look like stopping anytime soon.

However, his career has been marred by moments of heartbreak. Here are the top eight saddest moments in Leo’s career.

7. The 7-0 loss to Bayern Munich

It was one of the most embarrassing Barcelona nights in Messi’s career. The Blaugrana were dismantled both home and away by the German giants who went on to lift the Champions League trophy.

His sending off in his Argentina debut

In 2005, La Pulga was handed his Argentina debut. The Barca ace played for the senior side for the first time, coming in as a substitute against Hungary. 30 seconds later, he was sent off.

6. That penalty miss vs Chelsea

Leading 2-1 against 10-man Chelsea, Barca were awarded a penalty. Messi stepped up knowing he needed to score for his team to make the final, but smashed the ball into the bar. They drew 2-2 and crashed out of the tournament.

5. Crashing out of the Copa America last 8 on home soil

In 2011, hosts Argentina were shockingly eliminated from the Copa America in the quarter-final round by 10-man Uruguay.

4. Watching Cristiano win back-to-back Ballon d’Ors

After winning four-straight Ballon d’Ors from 2009 to 2013, he had to wait until 2016 to get his hands on the coveted prize. To make things worse, he had to watch rival Cristiano win it twice in a row.

3. His Copa final loss to Chile – the first one

In 2015, Messi appeared destined to end Argentina’s long wait for silverware when they faced Chile in the Copa America final. However, atrocious misses saw the game reach penalty shoot-out, which La Roja won.

2. His Copa final loss to Chile – the second one

A year after their previous defeat to Chile, Argentina faced them again – this time in Copa America Centenario. This game also went to shootout, with Messi missing from the spot en route to their defeat. This loss was so heartbreaking, it sent Leo into a temporary retirement.

1. The World Cup final defeat

This was probably the hardest loss. Nothing compares to winning the World Cup, and after reaching the final, Messi had a chance to join Maradona as an Argentine hero. Sadly they lost in extra-time, with Leo being handed the Golden Ball as consolidation.