Tonight’s Carabao Cup clash with Chelsea will be our 11th meeting in the competition with our capital rivals.
This evening’s fourth-round encounter, however, will be the earliest we have been drawn against the Blues in the League Cup, with each of our previous fixtures having come in the fifth round or later.
So, ahead of the west London outfit’s visit to N17 - for what will be the first EFL Cup tie to be held at Tottenham Hotspur Stadium - we take a look back at the first 10 matches between the two sides in the competition…
1971/72
22 December, 1971 - Chelsea 3-2 Spurs - Semi-final, first leg
We reached the semi-finals of the League Cup five times in our first nine participations in the competition, including this double header against Chelsea in 1971/72. Bill Nicholson’s side had negotiated a path to the last four by overcoming West Brom, Torquay United, Preston – after a replay – and Blackpool. Chelsea beat Plymouth Argyle, Nottingham Forest, Bolton and Norwich en route to the semi-finals and then edged a five-goal thriller in the first leg against us at Stamford Bridge.
The game saw two cup holders clash as Chelsea had won the European Cup Winners’ Cup the previous May while we lifted the League Cup by beating Aston Villa. It was our last match before Christmas and we fell behind when Pat Jennings and Terry Naylor collided on the edge of the area and Peter Osgood curled home the opening goal. But we responded well and levelled when Naylor headed in on 50 minutes, before taking the lead moments later through a superb Martin Chivers volley.
Chris Garland’s header restored parity however, before the Blues snatched a late winner after Naylor had handled in the area and John Hollins converted the penalty.
5 January, 1972 - Spurs 2-2 Chelsea - Semi-final, second leg
A second successive League Cup Final appearance for us was snatched away in the closing stages of the second leg at the Lane. Having gone ahead on the stroke of half-time thanks to another goal from Chivers, the visitors regained their aggregate lead on 62 minutes when Garland hit a powerful drive past Jennings.
With eight minutes remaining though, Alan Hudson was penalised for handball and Martin Peters scored from the spot to level it all up at 4-4. Extra time was looming but as the game entered its last minute, Hudson struck a low free-kick from out wide to the left of the area, Cyril Knowles took a swing of the ball but failed to connect, leaving Jennings wrong-footed as it trickled in at the far post to hand the Blues the 5-4 aggregate win. Chelsea lost 2-1 to Stoke City in the Wembley final.
1990/91
16 January, 1991 - Chelsea 0-0 Spurs - Fifth round
Another London derby awaited us in the fifth round of the Rumbelows Cup in 1990/91 as we were drawn away to Chelsea and looked to have the upper hand after holding the Blues to a goalless draw to force a replay back in N17.
We had to weather a Chelsea storm in the first half with goalkeeper Erik Thorstvedt making some crucial saves while Justin Edinburgh cleared off the line to keep the scores level. Gary Lineker and Paul Walsh had late opportunities to snatch the win, but neither side could break the deadlock and we reconvened at the Lane a week later.
23 January, 1991 - Spurs 0-3 Chelsea - Fifth round
For the second successive season we exited the competition at the fifth-round stage following a home defeat in a replay. Twelve months earlier it was Nottingham Forest doing the damage with a 3-2 win in north London, before Chelsea repeated the feat with a big derby victory.
We had penalty appeals waved away after Paul Gascoigne went crashing in the area following a typical mazy run before the Blues took control. Andy Townsend gave them a 16th minute lead, Kerry Dixon doubled their advantage in the 69th minute and the scoring was completed when Dennis Wise converted a penalty with seven minutes left.
Chelsea lost 5-1 on aggregate to Sheffield Wednesday in the semi-finals, with the Owls going on to win the cup against Manchester United in the final.
2001/02
9 January, 2002 - Chelsea 2-1 Spurs - Semi-final, first leg
Our next League Cup meeting with Chelsea came in the semi-finals of the 2001/02 tournament and this time it was us who came out on top.
The Blues held a narrow advantage after the first leg at Stamford Bridge. Jimmy Floyd Hasselbaink put them ahead in the 10th minute before Les Ferdinand latched onto Tim Sherwood’s pass to equalise 20 minutes into the second half. But with 13 minutes left, Ledley King was penalised for handball and Hasselbaink smashed home a 30-yard free-kick to give Chelsea a 2-1 win.
23 January, 2002 - Spurs 5-1 Chelsea - Semi-final, second leg
Having gone 12 years without beating Chelsea in all competitions, we emphatically ended that sequence with a thrilling victory at the Lane to book our place in the League Cup Final.
Glenn Hoddle’s side made the perfect start when Steffen Iversen capitalised on some hesitant defending from John Terry to open the scoring inside two minutes. We took the overall lead in the tie after 33 minutes thanks to Sherwood’s fierce half-volley and four minutes into the second half, Teddy Sheringham thumped home past future Spur Carlo Cudicini. Hasselbaink was dismissed for the Blues and we took full advantage, Simon Davies making it 4-0 on the night before substitute Sergei Rebrov added a fifth with four minutes left. Chelsea replied with a consolation goal from Mikael Forsell, but the party was already well under way!
We couldn’t finish the job in the final though, going down 2-1 to Blackburn Rovers at Cardiff’s Millennium Stadium.
2007/08
24 February, 2008 - Spurs 2-1 Chelsea - League Cup Final
We’d enjoyed a memorable 5-1 semi-final, second leg win over Arsenal at the Lane to book our date with Chelsea in the final of 2008 – and this time we made no mistake.
A bright start saw Robbie Keane go close inside the first minute and Pascal Chimbonda head against the bar, while Frank Lampard and Didier Drobga had chances for the Blues before the latter opened the scoring, curling a 20-yard free-kick past Paul Robinson on 39 minutes. Half-way through the second period, we levelled the scores. Wayne Bridge was adjudged to have handled in the area and Dimitar Berbatov was coolness personified as he rolled the resulting penalty past Petr Cech. Didier Zokora then had a chance to win the game, racing clear only for Cech to save before the midfielder sliced the rebound wide and the match headed to extra time.
Just four minutes into the additional half hour, Jermaine Jenas delivered a free-kick which Cech punched onto Woodgate’s head, the ball bouncing into the empty net. Despite some intense Chelsea pressure, we held out for the victory
2014/15
1 March, 2015 - Spurs 0-2 Chelsea - League Cup Final
Seven years later, the two teams met once again in the final but this time it was the Blues who took the honours to give Jose Mourinho his first trophy in his second spell as their manager.
We’d enjoyed a fine 5-3 defeat of Chelsea at White Hart Lane exactly two months earlier, but couldn’t repeat that performance at Wembley. Christian Eriksen hit the bar in the first half and Petr Cech kept out Harry Kane’s low shot, before Chelsea went ahead on the stroke of half-time, John Terry pouncing on a loose ball in the area following Willian’s free-kick to prod past Hugo Lloris.
Our hopes of a comeback were ended 11 minutes after the break when Diego Costa’s shot deflected off Kyle Walker and beat Lloris inside his near post to round off a disappointing afternoon for us.
2018/19
9 January, 2019 - Spurs 1-0 Chelsea - Semi-final, first leg
This was our third League Cup semi-final match-up with Chelsea and only a change in the competition rules prevented us from going through to another final appearance.
We had a run of local matches en route to the semi-final, starting with a ‘home’ game at Stadium MK against Watford in round three as our home base of Wembley Stadium was out of action. A penalty shoot-out victory saw us progress after a 2-2 draw before away wins at West Ham United and Arsenal set up this Chelsea clash.
Back at Wembley for the first leg, we stole a narrow advantage thanks to a Harry Kane penalty to give us something to fight for in the second leg in west London.
24 January, 2019 - Chelsea 2-1 Spurs - Semi-final, second leg
N'Golo Kante and Eden Hazard both scored to give the hosts the upper hand in a first half at Stamford Bridge in which we struggled to create chances but Fernando Llorente glanced in Danny Rose's cross to make it 2-1 on the night. It finished 2-2 on aggregate but instead of going to extra time – and in previous seasons we would have progressed on the away goals rule had it finished that way after 120 minutes – the new rules meant the game went straight to penalties.
The shootout didn’t go our way though as Eric Dier hammered over the bar and Lucas Moura was denied by Kepa Arrizabalaga to bring our cup journey to an end.