Throughout his tenure, Levy faced criticism despite significant milestones. Under his leadership, Tottenham finished as Champions League runners-up in the 2018–19 season and Premier League runners-up in the 2016–17 campaign. More recently, in May 2025, Spurs defeated Manchester United via an own goal to win the Europa League, securing a major trophy after decades.
Acknowledging domestic gaps, Levy admitted: "What I would have hoped for is winning the Premier League, winning the Champions League… easier said than done." He added: "Tottenham fans should be proud that the club has made such a fantastic contribution to the local population."