The 10 best Arsenal-Chelsea games: why left-backs have ruled

Mike Carre takes a trip down memory lane for the most entertaining Blues-Gunners clashes... 

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Feast your eyes on the below – and then relive the glory/heartbreak (delete as applicable)...

1. Chelsea 2-2 Arsenal, Mar 1973

Osgood was the last player to date to score in every round, and he scored an exceptional volley against Arsenal in this 1973 quarter-final tussle

Peter Osgood had a fairytale relationship with the FA Cup. Heartbreakingly, he missed Chelsea’s first-ever final in 1967 with a broken leg, before getting his happy ending in 1970’s FA Cup Final replay win over Leeds.

He’s also famous for two other FA Cup exploits with Chelsea: he was the last player to date to score in every round, and he scored an exceptional volley against Arsenal in this 1973 quarter-final tussle at Stamford Bridge.

The ‘King of Stamford Bridge’ volleyed into the far corner from the edge of the box – an eventual goal-of-the-season winner – to open the scoring in a game that finished 2-2, after Arsenal goals from Alan Ball and Charlie George were cancelled out by John Hollins' equaliser. Arsenal would win the replay 2-1, though, with strikes from Ball and Ray Kennedy. 

2. Arsenal 5-2 Chelsea, Apr 1979

Chelsea did pull one back but were relegated, manager Danny Blanchflower bluntly assessing: ‘I have a good club and a bad team’

Struggling Chelsea visited Highbury towards the end of the 1978/79 season knowing defeat would send them down. 

But a nightmare first half ended with them 2-0 down at the break courtesy of goals from David O’Leary and Frank Stapleton. Staring well and truly down the barrel, Chelsea’s Clive Walker halved the deficit halfway through the second half, but as the visitors chased the game, Arsenal sealed their fate when Alan Sunderland’s 80th-minute strike opened the floodgates. David Price netted a fourth before Stapleton completed his brace with five minutes left to make it 5-1.

Chelsea did pull one back through Tommy Langley but were relegated, manager Danny Blanchflower bluntly assessing: "I have a good club and a bad team." He left at the beginning of next season after just three wins in his 15 games in charge, and never masterminded from the dugout again. Maybe he should have added bad manager to his previous evaluation.

Blanchflower resigned shortly after relegation

Blanchflower resigned shortly after relegation

3. Chelsea 2-1 Arsenal, Feb 1991

Arsenal's unbeaten title-winning team of 2003/04 will forever go down in history, but that achievement could have been old news had Chelsea not beaten the Gunners in February of 1991, 23 years earlier, which proved to be their only one of the season as they won the title by seven points.

Chelsea seized control in the second half thanks largely to Nigel Winterburn and his torrid day

In a tight match, Chelsea seized control in the second half thanks largely to Nigel Winterburn and his torrid day. The left-back would go on to record probably his finest hour in the fixture six years later (more on that later), but this time around he cost his side dear.

His wayward header allowed Kerry Dixon to head into an almost unguarded net, and soon after the former Wimbledon defender inexplicably followed the ball to the opposite side of the pitch, leaving Graham Stuart completely unmarked at the back post for the simplest of tap-ins. Alan Smith’s clinical effort pulled one back but it was too little too late. Invincibility would have to wait.

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4. Chelsea 2-3 Arsenal, Sep 1997

You’ll notice a strange theme developing over this list of games, and here's the first case in point. Left-backs have influenced this rivalry long before Ashley Cole made his poisonous switch to Stamford Bridge, and Winterburn was among the first of many to come up with an unexpected and vital goal in this fixture.

Winterburn celebrates after doing something very un-Winterburnlike

Winterburn celebrates after doing something very un-Winterburnlike

The long-serving touchline dweller was hardly known for his goalscoring exploits but, for some reason, decided to let rip from all of 30 yards in the 88th minute of this classic to-and-froer that was delicately poised at 2-2 after Chelsea goals from Gus Poyet and Gianfranco Zola either side of a Dennis Bergkamp brace. Unbelievably, it found the far top corner and won the game for Arsenal against one of their nearest rivals as they went on to secure the title (and then FA Cup) for the first time under Arsene Wenger.

5. Chelsea 3-1 Arsenal, Feb 1998

Chelsea had sacked manager Ruud Gullit just days earlier and went into this League Cup semi-final second leg 2-1 down from the first leg at Highbury. 

But the Blues' turmoil mattered not as player-manager Gianluca Vialli would mastermind a stunning comeback in his first game in charge, ending Arsenal’s 12-game unbeaten run. It was a game of nine yellow cards, a spectacularly stupid red, and one particularly memorable goal.

It started well for Vialli before he fell out with everyone

It started well for Vialli before he fell out with everyone

Mark Hughes's twist-and-shoot opener got the Blues off to the perfect start, which got even better shortly after half-time when Patrick Vieira earned a second booking for needlessly hauling down Graeme Le Saux. It got worse for Arsenal. Just three minutes later a stunning long-range strike from Roberto Di Matteo put Chelsea in control, before Dan Petrescu wrapped things up with a smoothly taken goal.

Bergkamp's late consolation was futile as the Gunners crashed out, and ultimately missed out on being the first team to claim England's domestic treble after going on to win the Premier League and FA Cup.

6. Chelsea 2-3 Arsenal, Oct 1999

Nwankwo Kanu is something of a cult figure at every club he has played at, thanks largely to his unique style of play and happy-go-lucky nature. However, he cemented a far more valuable legacy with an exquisite 15-minute hat-trick at Stamford Bridge to inspire a famous Gunners comeback from 2-0 down. 

Kanu kick it... well, he can

Kanu kick it... well, he can

Chelsea thought they had the game all sewn up shortly after half-time when Petrescu added to Tore Andre Flo's goal six minutes before the interval. But Arsenal's Nigerian hero had other ideas. His first two goals owed it all to his cunning and delicate touch, but it's his 90th-minute winner that will really live long in the memory. 

Even after he'd chased down Albert Ferrer's stray clearance, it seemed the hosts could still cope with the lanky striker. But, dribbling past a stranded Ed de Goey, Kanu whipped the ball over an array of Chelsea defenders into the far top corner from an impossible angle, sending Sky Sports commentator Martin Tyler into a fit of excitement to screech the famous line: “Can you believe it?!”

7. Chelsea 2-2 Arsenal, Sep 2000

It's left-back time again, but this one features less Warwickshire and a bit more Brazil. The thought of a Samba left-back might make most Gunners cover their eyes after their Andre Santos debacle, but another former Corinthians man, Silvinho, was a far more reliable acquisition.

Silvinho makes Cudicini sad

Silvinho makes Cudicini sad

His crowning moment in a brief two-year stay at Highbury was a spectacular equaliser at Stamford Bridge to rescue a late point as Arsenal once again staged a comeback from 2-0 down. Goals either side of the break from Jimmy Floyd Hasselbaink and Zola had put the west Londoners in command, before Thierry Henry halved the deficit 15 minutes from time. 

Arsenal couldn’t quite repeat their trick of winning on this occasion but Silvinho did match Winterburn’s heroics, hammering home a ferocious left-footed strike from range to bamboozle Carlo Cudicini and earn Wenger's men a point. 

8. Arsenal 2-0 Chelsea, May 2002

An FA Cup final famous for two outstanding goals, one from Ray Parlour seconds after Chelsea fan and televisual Neanderthal Tim Lovejoy uttered the now-infamous words: “It's only Ray Parlour.”

Parlour was hardly a goal-getting midfielder – 22 in 400 league appearances says as much – but the Barking-born favourite produced a fine effort to elude Cudicini and give the Gunners the lead with 20 minutes remaining.

"It's only the FA Cup... right?"

"It's only the FA Cup... right?"

His goal won't be forgotten, but Parlour was outshone by Freddie Ljungberg for Arsenal's second after the Swede dribbled from inside his own half, left John Terry on his backside and bent a sumptuous strike into the far corner to seal the match, trophy and another double for the north Londoners.

9. Arsenal 1-2 Chelsea, Apr 2004

It's another instalment in our left-back series, although this time in Chelsea’s favour. Wayne Bridge’s Blues career wasn’t all that much to shout about, largely due to Cole’s arrival at Stamford Bridge, but he did get one up on his adversary before ‘welcoming’ him as a team-mate.

In the 2003/04 quarter-finals of the Champions League, this all-Premier League tussle was tied at 2-2 on aggregate with the game heading into extra-time. But Bridge, of all people, won it just minutes from the end, bursting into the box and finding the far corner.

Bridge over troubled water: Wayne does something memorable

Bridge over troubled water: Wayne does something memorable

Chelsea were beaten by Monaco at the next stage, but this goes down as Arsenal’s big opportunity missed in their ‘Invincibles’ season, with Jose Mourinho's Porto eventual finalists and winners.

10. Chelsea 3-5 Arsenal, Oct 2011

A fine game, but one played between two teams at their weakest for a number of years

An eight-goal thriller that epitomised both teams' 2011/12 campaigns. Chelsea, under Andre Villas-Boas, struggled with their Portuguese manager's determination to play a high defensive line, something that Robin van Persie exploited – typical in a 30-goal season in which he largely carried the Gunners.

In this game Arsenal twice came from behind (Andre Santos continued the left-back curse to level things up at 2-2), after Blues goals from Frank Lampard and Terry. However, Juan Mata’s free-kick levelled matters after Theo Walcott struck 10 minutes after half-time, but as Chelsea chased a winner, Terry's slip allowed Van Persie in on goal, and the Dutchman rounded Petr Cech to score with five minutes left. To make matters worse for the hosts, Van Persie completed his hat-trick in stoppage time with a thumping shot.

Van Persie celebrates his last-gap heroics

Van Persie celebrates his last-gap heroics

A fine game, but one played between two teams at their weakest for a number of years – Chelsea finished sixth (25 points behind winners Manchester City), while Arsenal clinched third on the final day of the season in a nervy afternoon at The Hawthorns. 


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