The new Everton winger becomes the last man to leave White Hart Lane from the matchday squad that beat AC Milan in the Champions League in 2011.
Aaron Lennon ended a ten-year stint at Tottenham on transfer deadline day, agreeing a permanent switch to Everton and marking the conclusion of a decade at White Hart Lane.
The diminutive winger has slipped down the attacking preferences at the North London club, but in his pomp the 28-year-old was one of Spurs’ best players.
For nostalgic Tottenham fans, Lennon’s sale will mark the end of an era, with the attacker the last member of the matchday squad that beat AC Milan at the San Siro back in 2011.
The White Hart Lane side’s holy grail is to qualify for the Champions League; the team have been trying to do so for years on end.
However, in the modern era Spurs have only competed in Europe’s top tournament for one campaign, in 2010-11, and captivated audiences with wins over both of the Milan teams.
Victory against the Rossoneri in early 2011 was the team’s final victory of the Champions League campaign, with Spurs failing to qualify since.
As such, with Lennon’s departure, Spurs no longer have a player in their midst that can claim to have won a game for the club in the Champions League - with the aim surely to change this as soon as possible.