Tottenham 2-1 Chelsea, Apr 1910
Going into this final-day encounter, both sides knew a win would keep them up. Spurs could also draw, being a point ahead of the Blues, who occupied the first of two relegation spots.
Ticket prices for this hotly-anticipated fixture were doubled, but that didn’t stop the Londoners turning up in their thousands - 40,000, in fact. A snippet from the matchday programme read: "The long, drawn-out struggle ends today. The climax has come and by this eventide all doubts and fears will be set at rest. This final match of 1909-10 must be as memorable as the last game of 1908-09. It is hardly possible to conceive of a more dramatic finish to a season than this which brings into conflict two great rivals when the prize at stake is of infinite importance to each."
Chelsea, who'd invested heavily in their squad in a late bid to save their campaign, took an early lead through James Windredge after five minutes. But Billy Minter levelled things for the hosts, and early in the second half Spurs won it through former Chelsea man Percy Humphreys, whose goal condemned his old employers to their first-ever relegation. A "dramatic struggle" noted the Daily Mirror.
Tottenham 2-1 Chelsea, May 1967
The first ever all-London FA Cup final, aptly named the Cockney Cup Final, drew over 100,000 fans to Wembley. Bill Nicholson’s four-time winners were confident, having landed the trophy twice in succession in 1961 and 1962, and captain Dave Mackay believed that his side were “unbeatable”.
Chelsea, meanwhile, were appearing in only their second major cup final. Off the back of a disappointing season, in which they finished ninth, the Blues came into the match with more hope than expectation of lifting the famous trophy. Indeed, the boys from White Hart Line duly delivered; goals from Jimmy Robertson and Frank Saul put Spurs two clear, with Bobby Tambling's 85th-minute strike a mere consolation.
"Tottenham, who in beating Chelsea on Saturday at Wembley infinitely more easily than the score would indicate, recorded their third success in the competition in seven years," hailed The Glasgow Herald.
Tottenham 2-0 Chelsea, Apr 1975
In Eddie McCreadie's first game in charge of cash-strapped Chelsea, his new side and Terry Neill’s Tottenham would again, just like in 1910, face off in a relegation crunch match. This time there were three matches of the campaign left, however, with Tottenham a point behind the Blues in the drop zone. With 51,000 crammed into White Hart Line and thousands of fans locked out, it was always going to be a game to remember.
At the time this was perhaps the most important game ever played between the two clubs. McCreadie's first big decision as boss was to appoint 18-year-old Ray Wilkins as captain for the game ("everyone thought I was a nutcase," he would later admit).
Unsavoury pre-match scuffles threatened to stop the game going ahead altogether. But go ahead it did, and McCreadie's refreshed Chelsea side fought hard. Eventually it was the home side's guile that came out on top, however, with second-half goals from Steve Perryman and Alfie Conn. Chelsea had seen two goals disallowed - and it would only get worse. The Blues drew their next two games at home to Sheffield United and Everton, going down a point behind Tottenham, who survived after one defeat and a win from their final two matches.
Chelsea bounced back two seasons later under McCreadie's stewardship, before he resigned after his request for a company car was turned down (and then granted, but too late) by chairman Brian Mears. "It wasn't for me, it wasn't for anyone else; the most important thing was getting the club back where they belonged," he said.
Chelsea 2-3 Tottenham, Mar 1982
Chelsea were relegated to the Second Division again in 1979, and hadn't met their London rivals for three-and-a-half years before this FA Cup quarter-final at Stamford Bridge.
Tottenham packed around 14,000 fans in the Blues' North Terrace and West Stand for the occasion, as they aimed to defend the trophy they'd won yet again the previous season. Having that many opposition fans caused problems, though - even before the game, Chelsea's matchday magazine was forced to print a warning on its usually-commemorative front cover, saying: "Due to the problems caused by a small lunatic fringe who persist on causing trouble for the club, we have been forced to alter the design in order to make the following statement." The warnings weren't heeded, though, and arrests were made.
Thankfully the game itself was memorable for the right reasons. Chelsea took the lead through a Mike Fillery free-kick, but Spurs were revitalised in the second half thanks to instrumental England star Glenn Hoddle. Goals from Steve Archibald, Mick Hazard (not Eden, obviously) and Hoddle himself - an arrowed finish into the bottom corner after cracking work from his team-mates - sent the Spurs faithful home happy.
There'd be more joy to come - Tottenham saw off Leicester in the semi-finals at Villa Park to tee up a Wembley showdown with London rivals QPR. Keith Burkinshaw's men earned a 1-1 draw after extra-time in the first game, but got the job done in the replay five days later when Hoddle's penalty won them a second successive FA Cup.
Tottenham 1-6 Chelsea, Dec 1997
The two sides' starts to the season could almost have been no more different; Tottenham were languishing in the bottom three after eight defeats from their first 16 games, while Chelsea occupied second place, three points behind Manchester United.
Naturally, the Blues were expected to continue their title bid at White Hart Lane - but perhaps not quite so emphatically. Tore Andre Flo netted the first five minutes before the interval, but Christian Gross's Spurs were back on level terms by half-time thanks to Ramon Vega.
This was only the north Londoners' third outing under their hapless Swiss boss, who'd turned up to his first press conference branshing a tube ticket and declared: "This is my Underground ticket. I came like the normal people come to the football club." His second home game went disastrously - Roberto Di Matteo second three minutes after the break, before Dan Petrescu, Flo and Mark Nicholls stretched the Blues' tally to five. Flo completed his hat-trick, and the rout, in the final minute.
Gross was retained until the following campaign before being sacked three games in. Chelsea finished fourth, well off the pace of winners Arsenal, while Tottenham eventually dragged themselves to 14th, after an almighty relegation scare.
Tottenham 2-2 Chelsea, May 1999
That fourth place was Chelsea's highest in the top tier since 1969/70 - and this time they had their sights properly set on the title. Going into this White Hart Lane tussle on the penultimate matchday of the season, the Blues were four points behind leaders Manchester United and knew only a win would keep their faint hopes alive.
Things started well when Gus Poyet finished in the fourth minute, but the hosts turned things around either side of half-time with goals from Steffen Iversen and David Ginola. Chelsea didn't lie down, however, and got themselves back in it thanks to Bjarne Goldbaek's piledriver with 18 minutes left. It might have been a goal worthy of winning the game, but it wasn't enough to do so here.
Had the Blues not fluffed their lines, there may well have been a three-horse race on the final day (with the three contenders on 76, 75 and 74 points respectively). Arsenal lost at Leeds the next day, while Man United were held to a goalless draw by Blackburn. Nevertheless, their draw knocked the west Londoners out of the race, and United beat Spurs on the final day to land the first trophy of their treble-winning campaign.
Tottenham 5-1 Chelsea, Jan 2002
Chelsea won the first leg of this League Cup semi-final 2-1 - but they wouldn't enjoy the second installment one bit.
Tottenham fans were made to wait for this victory over the Blues - they beaten their rivals since February 1990, having tried 26 times since - but this was worth it. Chelsea were expected to secure their route to the final, with Gianfranco Zola, Jimmy Floyd Hasselbaink and a young Frank Lampard at their disposal.
This, however, was a day when everything clicked for the hosts. Goals from Steffen Iversen and Tim Sherwood put Spurs in control by half-time, before Teddy Sheringham added a third after the break. Hasselbaink was sent off five minutes later, despite Mario Melchiot being the culprit, and then Simon Davies and Sergei Rebrov compiled the Blues' misery.
Annoyingly for Spurs, this was as good as it got for a fair old while. Not only did they go on to lose to Blackburn in the final, but they then failed to beat Chelsea in their next 10 meetings.
Still, at least Iversen’s opener was a peach...
Chelsea 2-1 Tottenham, Mar 2006
Everyone loves an injury-time winner - everyone except those on the receiving end, of course. Chelsea were romping towards successive titles under Jose Mourinho, 15 points clear of nearest challengers Manchester United with only 10 games to play. Tottenham, meanwhile, were hunting Champions League football, and a highest-ever Premier League finish to beat their previous best of seventh.
But this would be a cruel game for Martin Jol's men. They fell behind to Michael Essien's 14th-minute opener, but levelled things on the stroke of half-time through Jermaine Jenas. A point wouldn't have been the worst result for the north Londoners, and that's what they were headed for as the clock ticked past 90 minutes. It was not, however, the result they ended up with. In the 92nd minute, William Gallas decided to take matters into his own hands. Starting with the ball just inside the left touchline, the Frenchman burst past Paul Stalteri on the inside before unleashing an unstoppable beauty past Paul Robinson.
Chelsea won the title by eight points, while Spurs continued their fight for fourth. But then came Lasagne-gate, disastrous final-day defeat at West Ham and some very, very upset Spurs fans.
Tottenham 2-1 Chelsea, Feb 2008
The first League Cup final to be played at the new Wembley produced another Spurs victory against the odds.
Chelsea, despite having lost their crown to Manchester United the previous campaign, were perhaps the most dangerous team in the country under Avram Grant (no, seriously). So when Didier Drogba’s first half free-kick made him the first man to score three League Cup finals, it looked liked the Blues were on their way to their first piece of silverware of the season. But Wayne Bridge handled inside the area to gift Dimitar Berbatov an equalising penalty, which sent the game to extra-time. By that point it didn't matter how a goal went in, and in the end Jonathan Woodgate's fortuitous face-goal three minutes into the additional 30 gave Spurs their first piece of silverware in nine years.
It proved to be Juande Ramos’ only full season at the club. Grant's men, meanwhile, finished league runners-up behind United again, and were beaten by the Reds in that year's Champions League final on penalties.
Tottenham 1-5 Chelsea, Apr 2012
A thumping Blues win overshadowed by a controversial refereeing decision and yet more calls for goal-line technology.
Despite a strong start from Spurs, a blistering Didier Drogba net-buster opened the scoring for Chelsea three minutes before the break. After half-time came the controversy: Ledley King and Benoit Assou-Ekotto appeared to block Juan Mata's goal-bound effort on the line - but referee Martin Atkinson gave a goal. Understandably riled, Spurs hit back through Gareth Bale, but succumbed to goals from Ramires, Frank Lampard - a stunning free-kick - and sub Florent Malouda.
