On Thursday, the Lilywhites get the chance to avenge their 2015 League Cup final defeat at the hands of the Blues and dump the Chelsea boys out of the competition at the semi-final stage.
Harry Kane’s first half Wembley penalty has given Spurs a slender 1-0 advantage as they head to Stamford Bridge looking to take a step closer to their first trophy since 2008.
However, injury has ruled out the talisman as well as host of first teamers including Son Heung-min.
With so much on the line, can the Lilywhites hold on and reach (err) Wembley and finally break their decade long trophy hoodoo?
Who Will Mauricio Pochettino Play Up Front?
In the weekend win over Fulham, Spaniard Fernando Llorente was trusted with the responsibility of leading the line and he got on the score sheet.
Unfortunately, it was for Fulham as 17th minute own goal gave the Cottagers a half-time lead.
However, the veteran is still a class act and there is every reason to believe he will take to the pitch at Stamford Bridge.
After all, Spurs don’t need to win the game, just avoid defeat and they are through.
Tottenham are seeking their first League Cup triumph since defeating Chelsea in the 2008 final 2-1.
It is ironic then that the last time Chelsea won the competition in 2015, they beat Tottenham in the final.
The pair clearly have a history of meeting one another as this will be the tenth contest between Chelsea and Tottenham in the League Cup.
However, this season, Tottenham have not had to leave the city of London having dismissed Watford, West Ham, and Arsenal on their way to the semi-final.
Chelsea themselves has only left the capital once in the competition this season when they travelled to Anfield and defeated Liverpool 2-1.
Two home ties have since followed against Derby and Bournemouth respectively.
Who Will Win?
No easy prediction this one, but the ball is firmly in Tottenham’s court.
A draw is all the Lilywhites need and with no solid replacement for Kane, there is every chance Pochettino will opt for a defence minded approach.
Spurs won on their last visit to the Bridge in an April 2018 Premier League clash, but this game is an entirely different proposition.
Backing the draw makes sense in this one as that will leave the Lilywhites dancing all the way to the final to take on Manchester City.