Tottenham 5-1 Chelsea, League Cup semi-final (2002)
In terms of margin of victory, this was Tottenham’s biggest success against their London rivals since a 4-0 triumph in 1958. Trailing 2-1 from the first leg of this League Cup semi-final, Spurs turned on the style in front of their own fans at White Hart Lane to set up a Wembley showpiece against Blackburn Rovers.
Steffen Iversen fired the home side in front with less than two minutes on the clock, before Tim Sherwood and Teddy Sheringham extended Tottenham’s lead either side of half-time. Goals from Simon Davies and Serhiy Rebrov were the icing on the cake, with Mikael Forssell’s 89th-minute effort nothing more than a consolation.
Chelsea 3-3 Tottenham, FA Cup quarter-final (2007)
A thrilling clash at Stamford Bridge ended with the scores level in this FA Cup quarter-final, forcing a replay which was won by Chelsea.
Tottenham drew first blood in the initial meeting, Dimitar Berbatov hammering the ball past Petr Cech in the fifth minute, but Frank Lampard made it 1-1 midway through the first half. A Michael Essien own goal and Hossam Ghaly strike put Spurs in a commanding position before the interval, but Lampard and Salomon Kalou were on target in the second period to deny the north Londoners their first win at the Bridge since 1990.
Chelsea 1-2 Tottenham, League Cup final (2008)
Tottenham’s last trophy was won in 2008, when they beat Chelsea in the League Cup final at Wembley. Didier Drogba once again proved himself to be the man for big occasion by putting the west Londoners in front after 39 minutes, but Spurs regrouped impressively after the break to turn the match on its head.
First, Berbatov’s penalty restored parity after Wayne Bridge had handled the ball inside the 18-yard box, and although there were no more goals before the end of the 90 minutes, Jonathan Woodgate made himself a hero by nodding home the winner in the first period of extra time.
Chelsea 2-0 Tottenham, League Cup final (2015)
Mauricio Pochettino went close to winning silverware in his debut campaign at White Hart Lane, but Jose Mourinho’s Chelsea got the better of his Spurs side in the League Cup final.
John Terry broke the deadlock on the stroke of half-time to give the Blues the upper hand, before Diego Costa doubled their lead in the 56th minute. Mourinho’s side did an excellent job of shutting the game down from that point onwards, as a young Spurs team featuring Harry Kane, Christian Eriksen and Eric Dier struggled to penetrate their opponents’ backline.
Chelsea 4-2 Tottenham, FA Cup semi-final (2017)
With Chelsea’s lead at the top of the Premier League table having recently been cut to four points, Antonio Conte made a big call by leaving Eden Hazard and Diego Costa on the bench for his team’s FA Cup semi-final clash with Tottenham. It was a gamble that ultimately paid off, as the Blues ran out 4-2 winners in a pulsating encounter at Wembley.
Chelsea took the lead through Willian in the fifth minute, before Harry Kane levelled the scores in the 18th. Conte’s men re-established their one-goal advantage shortly before the interval, Willian scoring his second from the penalty spot, but Spurs again hit back through Dele Alli in the 52nd minute.
Conte turned to Hazard and Costa on the hour mark, and the former made it 3-2 with 15 minutes left on the clock. Tottenham pushed for another equaliser, but Nemanja Matic put the tie beyond them with a stunning strike from 30 yards.