It’s that time of the year again. No, not Christmas – the time of the season where we get to take on one of our biggest rivals in a match that is guaranteed to ruffle a few feathers. 

Not only will we be clinging on to our fourth-place spot, we’ll also be facing a man who knows our club pretty well.

But enough about Sunday. What about some of the past matches that have made this fixture so tasty? 

Chelsea 4-3 Tottenham (1994)

When Glenn Hoddle was player-manager of Chelsea, the Blues secured a 4-3 victory against his old side. The Spurs legend, who attracted the likes of Ruud Gullit and Gianfranco Zola to the club, witnessed a dramatic London derby as Chelsea managed one of the greatest comebacks in history.

Tottenham were experiencing a terrible league run and as a result, were desperate for a win. After just 20 minutes, they were already 2-0 up but Chelsea were able to get one back just before the half hour mark with a goal from Mal Donaghy. The comeback was on. Just four minutes later, the score was 2-2 as Mark Stein managed to net one back from a corner. Before the half time whistle blew, John Spencer scored another, sending Chelsea ahead for the first time in the match with the score currently 3-2 to the Blues.

After the break, there was another twist in store. Spurs were awarded a penalty after a handball by Erland Johsen – putting the score 3-3 as substitute Andy Gray scored from the spot. Just when you thought the drama was over, Spurs were handed another after Chelsea keeper Dmitri Kharine took down Ronny Rosenthal in the box. Gray steps up again and misses, sending Stamford Bridge into chaos. In stoppage time, another penalty was awarded – this time to Chelsea as Dean Austin fouls Gavin Peacock. Stein takes a massive run up and – you guessed it- hits the ball into the back of the net with a powerful strike. It’s a sigh of relief for the Chelsea fans as the Spurs supporters leave the ground with their heads in their hands, shocked at how they had given away such a convincing lead.

Tottenham 1-6 Chelsea (1997)

Back in 1997, it was Tore Andre Flo who stole the spotlight for the Blues. During their biggest ever win against the Lilywhites, the Norwegian managed to net a hattrick as Chelsea went on to beat Tottenham 6-1 in their own backyard. Flo started off the scoring with a fine header, before Ramon Vega equalised just three minutes later – setting the score 1-1 at half time.

However, the boys in blue were only just getting started as goals from Roberto Di Matteo, Dan Petrescu and Mark Nicholls all came flourishing through in the second half. Flo also got another two goals in the latter stages of the game, securing his hattrick just before the final whistle. 

It was a day to forget for Spurs fans as they were completely humiliated by Chelsea at White Hart Lane, with a gleaming Ruud Gullit looking on proudly from the sidelines.

Chelsea 3-3 Tottenham (2007)

Another dramatic comeback was Chelsea’s 3-3 draw against Spurs, earning them an FA Cup quarter-final replay under ex boss Jose Mourinho. Dimitar Berbatov started the goalscoring early by smashing one past Petr Cech in the first five minutes. However, the Blues managed to get one back when Frank Lampard turned in Micheal Ballack’s shot. Then disaster struck as Micheal Essien scored an own goal before Hossam Ghaly netted in another for Spurs, setting the scoreline as 3-1 before half time. The comeback looked out of reach for Chelsea but towards the latter stages of the game, things started to look positive for the home side…

After a superb save from Cech to deny Lennon, Lampard managed to pull one back from a close-range volley, sending the ball into the corner. With just five minutes left to play, it was Salomon Kalou who netted home the equaliser. 

Chelsea were given another fright as Jermain Defoe hit the crossbar late in stoppage time. Yet the scored ended 3-3, continuing Tottenham’s horrific record at Stamford Bridge. 

Chelsea 2-2 Tottenham (2016)

A 2-2 scoreline seems like an average game to the outside world, yet this battle at the bridge was anything but. Chelsea knew that bagging a point against their London rivals would demolish any chance they had of lifting the Premier League title in the 15/16 campaign – and that’s exactly what they did, handing the trophy over to Leicester in the process.

The Blues were off to a bad start with Harry Kane and Son Heung-min both scoring in the first half of the match. Tensions were already flying high – with an incident between Willian and Danny Rose taking place shortly before half time, resulting in a minor scuffle as Mauricio Pochettino stepped onto the pitch to separate the two sides. 

Guus Hiddink brought Eden Hazard off the bench at the beginning of the second half with the Blues determined to prevent a Spurs win. Chelsea were provided with a glimmer of hope as Gary Cahill hit the back of the net after 57 minutes. Then the real magic happened. Hazard curled the ball into the top right corner of the net. Approximately five minutes were left of the game and after nine yellow cards were shown to Tottenham (the record for a single team), the final whistle blew. Chelsea had done it – they had prevented Spurs from winning the tile in one of the most chaotic games in history.

Chelsea 2-1 Tottenham (2019)

What’s a top 5 list without rounding it off with a penalty shootout, eh? Despite this game only taking place earlier this year, it was full of twists and turns. Going into the match, Spurs were already winning 1-0 on aggregate, given them the much-needed lead against Chelsea as they headed to Stamford Bridge for the second leg of the Carabao Cup semi-final.

N’Golo Kante’s super strike from outside the box gave the Blues the lead after 27 minutes. Eden Hazard then scored a minute later, hoping that he had successful turned this semi-final around. However, a second half goal by Fernando Llorente, following a tactical switch by Mauricio Pochettino, meant the game was up for grabs for both teams once more.

After a set of close chances from both sides with either failing to hit the back of the net, the game was taken to penalties. That day, Kepa Arrizabalaga became the rightful hero – denying Lucas Moura from the penalty spot. Chelsea won the shootout 4-2 and were sent to the final to take on Manchester City. Although, we won’t remind you how that one went down.