Harry Kane's long wait for silverware was meant to come to an end this season as he signed for a Bayern Munich side that had won 11 straight Bundesliga titles.

But having slipped 10 points behind Bayer Leverkusen at the top of the league, the Champions League remains Kane's last realistic chance to finally get his hands on a trophy this season — at club level at least.

Ahead of Bayern's last-16 second leg against Lazio, we remember five occasions when the Premier League's second-highest all-time goalscorer came closest to breaking his duck.

2015-16 Premier League

As the team that ran shock champions Leicester closest in the 2015-16 season, Tottenham must reflect on a missed opportunity to lift a maiden Premier League title of their own.

Mauricio Pochettino's side played some fantastic football that year, inspired by Kane's Golden Boot-winning haul of 25 goals.

But they capitulated when they needed to deliver most, losing at home to the Foxes before later drawing at home to West Brom and blowing up in a 2-2 draw with Chelsea dubbed the Battle of the Bridge.

2019 Champions League final

Kane had missed the dramatic semi-final comeback against Ajax that saw Tottenham make the final and then replaced Amsterdam hat-trick hero Lucas Moura in the line-up.

But though the narrative goes that he was not really fit to start, Spurs were up against it here before the game even got going.

Liverpool went ahead from the spot after two minutes when Moussa Sissoko was harshly judged to have handled.

Pochettino's side gave as good as they'd got from then on but were ultimately beaten by a better team.

2021 Carabao Cup final

Seemingly unable to prepare for a final without some form of disruption, Tottenham sacked manager Jose Mourinho less than a week before the 2021 Carabao Cup showpiece against Manchester City.

The Portguese's tenure had become toxic in the preceding months and Spurs hung on in there against Pep Guardiola's side under the leadership of Ryan Mason at Wembley.

Aymeric Laporte's late header won it for the Citizens and Kane has not featured in a club cup final since.

Euro 2020 final

The following summer was the first of two big misses for Kane on the international scene.

England's skipper had netted in each of the knockout rounds to lead the Three Lions into the Euro 2020 final at Wembley, where his side led for much of the contest thanks to Luke Shaw's opener.

Eventually pegged back, the No9 converted from the spot during the penalty shoot-out but later misses denied him his moment of glory.

2022 World Cup quarter-final

Less than 18 months later, Kane had to shoulder more personal responsibility for the World Cup quarter-final exit to France.

Having already dispatched one penalty past then club team-mate Hugo Lloris, he sent a second — which would have taken the game to 2-2 with six minutes remaining — into Row Z.

With a depleted Morocco waiting in the semi-finals, a 2-1 defeat robbed Kane of a clear shot at lifting the iconic trophy.