Tottenham’s Harry Kane has set an unwanted record as his side crashed out with a whimper against AC Milan courtesy of a 0-0 draw in the second leg in north London.
With the tie intriguingly poised at 1-0 from the first leg, it seemed as though the odds may slightly favour Tottenham despite being a goal down, with the home crowd behind them as they sought to reach their first Champions League quarter-final since 2019.
What followed, however, was a dire performance that had fans leaving early even with just one goal needed, and boos ringing around the stadium at half time and full time, with a 0-0 draw enough to see the Italian champions into the last eight.
There were plenty of question marks over Antonio Conte’s decision making too, with a red card for Cristian Romero seeing the Italian opt to bring on Davinson Sanchez on for attacker Dejan Kulusevski, despite his side needing a goal to stay in the tie.
And as if to further demonstrate just how poor the Lilywhites had been this campaign, it has since emerged that Kane, who has relied upon by countless Tottenham managers, set a new record.
It is the first time in the Englishman’s career that he has finished a Champions League campaign without a non-penalty goal to his name, and just the second time he has done so in any European competition across his career to date.
The result leaves Tottenham with little left to fight for this season, having also crashed out of the FA Cup to Sheffield United in the fifth round, meaning that their trophy drought will stretch for another year.
And, with Antonio Conte out of contract this summer, and Harry Kane set to be out of contract in 2024, there could be major changes in north London.