Jan Oblak denied Ronaldo from the penalty spot during Monday’s last-16 clash between Portugal and Slovenia.

Lionel Messi and Cristiano Ronaldo are two of the highest scorers in football history but two goalkeepers got the better of them both from the penalty spot.

Portugal progressed to the last eight of Euro 2024 with a dramatic penalty shoot-out victory against Slovenia but it was Ronaldo who stole the headlines after breaking down in tears during extra-time.

Ronaldo was denied from the spot by Jan Oblak but confidently stepped up in the shoot-out to make amends for his earlier miss.

As always, the Al Nassr star is always compared to Messi given their status as two of the greatest players in football history and their penalty record is no different.

On the international stage, Messi boasts a penalty conversion rate of 82.8 per cent after converting 24 out of 29, while Ronaldo has recorded a success rate of 71.4%, scoring 20 out of 28.

The former Barcelona man also knows the pain of missing a spot kick against Oblak after the Atletico Madrid man kept out his penalty in the Copa del Rey quarter-final in 2015.

Oblak smartly read his run up to deny him from 12 yards but Messi had the last laugh with the rebound falling for the Argentine to smash home. Prior to his miss on Monday night, Ronaldo had a perfect record against Oblak, scoring on three other occasions.

That is not the case for the only other goalkeeper to deny both Messi and Ronaldo from the spot – with Ronaldo missing three out of the four he took against his bogey goalkeeper.

Ronaldo’s nemesis was former Valencia shot-stopper Diego Alves. The Brazilian saved a Ronaldo penalty in his debut season, and again in 2015 as well as 2017. Alves is responsible for saving 10% of Ronaldo’s missed penalties in his entire career.

The Portuguese isn’t the only one to suffer against Alves though, with Messi also failing to beat him from the spot. Alves denied the legendary forward in the 2012 Copa del Rey semi-final but again had the last laugh, knocking Valencia out before hammering Athletic Bilbao in the final.

Diego Alves saved penalties from both Lionel Messi and Cristiano Ronaldo (Getty)

In the past, Messi has stated his desire to increase his success rate from 12 yards.

“I would like to be more effective from the penalty spot,” Messi told Catalunya Radio back in 2018.

“But it’s difficult to work on penalties. It’s not the same taking them in training as it is in a game. You can have an idea in your head or something you have worked on, but it’s more difficult than it seems.

“The goalkeeper has a lot to do with it, too. If they guess right, they save it. But it’s obvious that I’d like to get better at taking penalties.”