Cristiano Ronaldo vs Lionel Messi: Who has gone longest without winning trophy?

Ronaldo and Messi have enjoyed unprecedented success in their career.

Lionel Messi and Cristiano Ronaldo have been the two cornerstones of football greatness for almost twenty years. Their rivalry shaped an age where success was measured not only in goals but also in trophies, spanning leagues and generations.

However, as both superstars continue their rivalry away from the well-known lights of Europe, an intriguing question arises: who of the two has gone the longest without winning a club trophy?

Even their most loyal fans are taken aback by this question, which conceals a record that few would equate with Ronaldo, the man who was previously known for his unending victories.

A new golden era seemed to begin when Cristiano Ronaldo joined Al-Nassr in January 2023. With a record that included five UEFA Champions League wins, seven league titles, and a legacy of supremacy at Manchester to Madrid and Turin, the five-time Ballon d’Or winner came to Saudi Arabia as the face of the country’s soccer transition.

However, the story has taken an unexpected turn after almost three years. Despite his many goals and international recognition, Ronaldo’s time in the Middle East has been characterised by something unfamiliar to him: defeat.

Since when has Ronaldo not won a trophy?

In the King’s Cup Round of 16, Al-Nassr lost 2-1 to Al-Ittihad on October 28, 2025, prolonging Ronaldo’s career’s longest club title drought. The evening ended with sadness once more, even though they created opportunities and helped Angelo Gabriel equalise.

It has been 1,623 days since Ronaldo’s last club championship. For one of soccer’s most illustrious players, that ultimate victory occurred on May 19, 2021, when Juventus defeated Atalanta 2-1 in the Coppa Italia final.

Since then, Cristiano Ronaldo has participated in 13 official competitions, losing each one while playing for Juventus, Manchester United, and Al-Nassr. His best chance at triumph came in 2024, when Al-Nassr lost to Al-Hilal on penalties in the King’s Cup final. He then suffered heartbreaking Super Cup losses in back-to-back years.

Since when has Messi not won a trophy?

Lionel Messi has managed to win titles practically everywhere he has gone, while Ronaldo struggles with near misses in Riyadh. Messi was almost unbeatable in his 17 years with Barcelona’s first squad, winning 35 club trophies, including 10 LaLiga crowns and four UEFA Champions Leagues.

Even his periods of dryness were brief. ESPN claim that Lionel Messi’s club career only has two trophy-less seasons: 2013–14 and 2019–20. Both had quick recoveries, including a treble in 2014–15 and another domestic trophy in 2020–21. Each drought lasted less than a year.

For more updates, follow Khel Now on Facebook, Twitter, and Instagram; download the Khel Now Android App or IOS App and join our community on Telegram.