Tottenham are just three matches away from lifting a first trophy in 16 years as a host of former stars continue to claim silverware.
Spurs host reigning Carabao Cup champions Liverpool in the first leg of their semi-final this week, live on talkSPORT, hoping to emulate their 2008 triumph in this competition.
Spurs beat Manchester United in a seven-goal thriller to progress to the last four,and the last time they beat the League Cup holders they won the trophy – with that 2-1 extra-time victory over Chelsea.
Returning the glory days to the Lilywhites is becoming a manner of desperation for Ange Postecoglou.
Their lengthy drought continues to be put in sharp relief by an ongoing trend of former employees enjoying success after leaving.
Emerson Royal became the latest former Tottenham player to have secured a winners’ medal since leaving north London.
The Brazilian defender started AC Milan’s 3-2 triumph over city rivals Inter in the Supercoppa Italiana in Saudi Arabia on Monday.
To add insult to injury, the only ex-Spurs star the fanbase would want to win trophies above the rest hasn’t in club legend Harry Kane.
Kane was in the Spurs youth ranks when the club last lifted a trophy – the 2008 League Cup – but has never won a major honour himself.
He is already Tottenham and England’s record goalscorer but the debate over his lack of medals blots his otherwise superb record.
After joining Bayern Munich, the striker missed out on a trophy in his debut season after the Bavarians endured their first trophyless season since the 2011–12 campaign – and then lost his second successive European Championship final in the summer.
