The 4 Times that Harry Kane Almost Won a Trophy at Tottenham

Kane doesn’t need a trophy to be a Tottenham legend, yet it is worth checking to see how close he came to claiming silverware in north London.

In one of the most exciting transfers of the summer, Harry Kane completed a €100 million move to Bayern ahead of the 2023-24 season, bidding farewell to his long-standing club, Tottenham.

As we look back on his time with the Spurs, there were four memorable occasions when Kane came close to clinching a trophy but fell just short.

2015 League Cup Final

Kane and his Spurs teammates came one step away from winning the Carabao Cup title after a thrilling run in the 2014-15 campaign. Fresh from a victory against Chelsea on New Year’s Day, Tottenham faced their city rivals with renewed confidence. Kane played a pivotal role, winning a crucial free-kick that rattled the crossbar. Despite promising chances for Nacer Chadli and Ryan Mason, Tottenham lost the game 2-0 as goals from John Terry and Diego Costa, both deflected, secured Chelsea’s victory. Kane’s unfortunate deflection of Terry’s strike only added to the disappointment as the English star’s wait for his first trophy continued.

2021 League Cup Final

Under the guidance of Jose Mourinho, Tottenham reached the 2021 EFL Cup final against Manchester City. However, Kane’s hopes of lifting the trophy were dashed by an injury that cast doubt over his participation. Following Mourinho’s controversial sacking, interim manager Ryan Mason took the reigns, but Kane’s fitness remained a question mark. Despite his presence on the pitch, the striker struggled to make an impact, registering no shots, key passes, or fouls. Ultimately, Tottenham lost the game 2-0 as they ended another season without winning silverware.

2016-17 Premier League Season

During the 2016-17 Premier League campaign, Kane’s exceptional goal-scoring qualities were on full display. He managed to score an impressive 29 goals in the league, claiming the league’s Golden Boot. Tottenham’s bid for the title was fierce, but the team fell short, finishing second behind Chelsea. Kane’s remarkable individual performance was a silver lining in a season that solidified his status as one of the league’s all-time great strikers.

2019 Champions League Final

One of the most painful near-misses for Kane and Tottenham came in the 2019 Champions League final against Liverpool. After battling injuries, the Tottenham striker returned to the lineup for the final. However, his presence on the pitch was largely ineffective, as Liverpool secured a 2-0 win. The decision to start Kane over other attacking options became a subject of debate as the English star failed to live up to expectations against Liverpool.