Kane, Le Tissier, Di Natale: Who is the best footballer never to win a trophy?

Tottenham and Harry Kane are out of the FA Cup after crashing out to Championship side, Middlesbrough, on Tuesday night.

It means it’s guaranteed to be another trophyless season for Spurs.

It also means that Kane, who turns 29 in the summer, is still looking for the first trophy of his career.

He may be one of the greatest strikers the Premier League has ever seen but Kane has suffered heartbreak in his career when it comes to winning trophies.

He’s finished runner-up in two League Cup finals, a Champions League final and the European Championships.

Is he the greatest ever player not to win a trophy in his career?

Of course, there’s every chance that Kane will still get his hands on a few honours before he retires – especially if he moves to Manchester City in the summer.

But to mark another trophyless campaign for him, we wanted to look back at some of the best players to have played the game and never won a major trophy.

Let’s take a look:

QUIZ: Can you name the footballer based on their Wikipedia page?

Di Natale was a proper goalscorer, bagging 227 goals in 446 matches for Udinese. He also represented Italy on 42 occasions, scoring 11 times.

But with only two permanent clubs – Empoli and Udinese – he didn’t stand much chance of winning a club honour while he missed out on a place at the 2006 World Cup. He did play in the Euro 2012 final but lost 4-0 to Spain.

From one brilliant Italian striker to another. Signori scored more than 250 goals during his career at the likes of Lazio and Bologna. If he had stayed at Lazio for three more years, he’d have won the Coppa Italia, Cup Winners’ Cup, UEFA Super Cup and Serie A title.

On the international stage, he scored seven times and was an unused substitute in the 1994 World