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Best and Worst Chelsea FA Cup Performances Against Lower-League Sides Since 1990

Garry HayesJan 3, 2015

The new year is here, and as tradition dictates, the first weekend of January is all about the FA Cup.

In keeping with the romance of the world's oldest cup competition, plenty of the Premier League's big guns have been drawn against lower-league opposition, including Chelsea, who will entertain Watford at Stamford Bridge.

These two clubs are familiar cup opponents, having faced each other four times in the past decade.

Chelsea have been the dominant force, though, winning three of those matches and drawing the other.

It hasn't always been that way down the years, with Chelsea being on the receiving end of some upsets.

Paying homage to to the Blues' recent history in the FA Cup, Bleacher Report looks at some of Chelsea's best and worst performances against lower-league opponents in the competition since 1990.

Worst: Bristol City 3-1 Chelsea (1990)

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Chelsea were enjoying their first season back in English football's top flight in 1989/90, while Bristol City were en route to promotion from Division Three (now League 1) with their city rivals Bristol Rovers.

That was no excuse for a poor display from Bobby Campbell's side, however, and they crashed to 3-1 defeat at Ashton Gate in the fourth round of the FA Cup

Watching the YouTube clip above, goalkeeping errors like the one Dave Beasant made for Bristol City's opener shows what kind of an afternoon it was for Chelsea.

Kevin Wilson scored for the Blues, while Mark Gavin and a Robert Turner brace gave the Robins a well-earned victory.

The cup upset came bang in the middle of a seven-game winning run for Bristol City, but they were knocked out in the next round, losing 5-1 to Cambridge United.

Best: Chelsea 2-0 Luton Town (1994)

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Chelsea returned to Wembley for an FA Cup game for the first time in 24 years in 1994, facing Luton Town in the semi-final.

With Kerry Dixon lining up for the Hatters against his former club, this game had banana skin written all over it.

Under Glenn Hoddle, Chelsea were beginning to emerge as a club with ambitions of going on to greatness, though, and they made no mistake here.

Gavin Peacock scored both goals in a 2-0 win, and although Chelsea lost to Manchester United in the final a few weeks later, this was the beginning of their journey to becoming the club we know today.

Worst: Chelsea 1-3 Oxford United (1991)

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If losing to Bristol City a year earlier wasn't bad enough, Chelsea's FA Cup hopes were again ended early by lower-league opposition in 1991.

This time, it was Oxford United, then of Division Two (now the Championship), who were the giant killers.

To make matters worse, Chelsea's humbling came at home.

Kerry Dixon scored for the Blues, but it was goals from Jim Magilton, John Durnin and Lee Nogan that gave Oxford fans a memory to cherish.

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Best: Portsmouth 1-4 Chelsea (1997)

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When Chelsea came back from two goals down to beat Liverpool 4-2 in the fourth round of the 1996/97 FA Cup, there was a feeling their name was on the trophy.

And so it proved.

Traveling to face Portsmouth at Fratton Park for the quarter-final was a big test of their cup credentials, however.

Pompey had just knocked Leeds United out in the previous round, and with a passionate crowd behind them—not to mention a cloud of sea mist dumping itself on the stadium just in time for kick-off—they were ready to pull off another upset.

With characters such as Mark Hughes and Dennis Wise in the line-up, Chelsea were having none of it, and the Blues came away with a comfortable victory.

It was impressive stuff as Hughes, Wise (two) and Gianfranco Zola scored for Chelsea. Deon Burton got a late consolation for the home side.

Worst: Chelsea 1-1 Millwall (1995)

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After drawing the first game of this FA Cup fourth-round tie, 0-0, the replay at Stamford Bridge was supposed to be a routine win for Chelsea.

Millwall were in Division One at the time, and with Glenn Hoddle's Blues going strong in the Cup Winners' Cup, their pedigree was expected to prove too much.

The Lions, inspired by the opportunity of getting one over on their fierce London rivals, didn't read the script.

It finished 1-1 after 120 minutes of play—Mark Stein scored for Chelsea, and Dave Savage notched for Millwall—meaning it would be decided by penalties.

Millwall scored all five of their spot-kicks, leaving it up to Kasey Keller and John Spencer to decide the game.

The goalkeeper came out on top, saving from Chelsea's diminutive Scot, dumping Chelsea out in the process.

As the YouTube clip above shows, after that penalty save, there were ugly scenes of violence between both sets of fans, making the night even more regrettable for Chelsea.

In the 20 years since, the clubs have yet to face each other again.

Best: Hull City 1-6 Chelsea (1999)

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This game is remembered for many things, notably the convincing scoreline—but also Gus Poyet's sublime opener.

The Uruguayan scored a wonderful long-range effort that few goalkeepers would have saved, looping over the helpless Hull City stopper.

As the news report states, this was a potential banana skin for Chelsea, traveling to Humberside to face a club with a reputation for giving top-flight clubs a hard time.

It was fairly routine, though, and Chris Sutton even found himself on the scoresheet, scoring one of his three goals in a Chelsea shirt.

Worst: Oxford United 1-1 Chelsea (1999)

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Here we go, it's Oxford United again.

Unlike in 1991, when they beat Chelsea 3-1 at Stamford Bridge in the FA Cup, the Us couldn't go all the way to record a famous victory against Chelsea, but they came mightily close.

Dean Windass put them ahead early in the second half, and after a poor display from Gianluca Vialli's side, it seemed as though that would prove enough.

But disaster struck in the 90th minute when the referee awarded a penalty for a lunge on the Chelsea player-manager.

As you'll see from the video above, it was actually a fair challenge by striker Kevin Francis.

After the controversy, it was left up to Frank Leboeuf to spare his team-mates' blushes, which he did, making no mistake from 12 yards to draw the game level at 1-1.

The replay at Stamford Bridge saw Oxford score an early opening goal, but Chelsea came back to win the tie, 4-2.

Best: Chelsea 6-1 Macclesfield Town (2007)

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The one and only time Macclesfield Town have faced Chelsea in their history soon became a nightmare for the Silkmen.

Chelsea showed their superiority with a dominant display at Stamford Bridge, thrashing them 6-1.

Frank Lampard scored a hat-trick, with Shaun Wright-Phillips, John Obi Mikel and Ricardo Carvalho completed the rout.

Macclesfield did briefly draw level when John Murphy equalised on 40 minutes, but his strike eventually proved to be nothing more than a consolation.

Worst: Barnsley 1-0 Chelsea (2008)

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With a team crammed full of international talent, cup upsets against lower-league opponents have become rare for Chelsea.

That said, they can still happen, as they found out in 2008 when they traveled north to face Barnsley.

It had been a strange season for Chelsea after Jose Mourinho's departure early in the campaign, being replaced by the unpopular Avram Grant.

Their league form was patchy, but in the cups, Chelsea seemed to be going strong.

It was a shocking performance against the Tykes, however, and they paid price for some sloppy defending when Kayode Odejayi scored just after the hour.

Despite fielding a team including Michael Ballack, Nicolas Anelka, Joe Cole and Michael Essien, Chelsea couldn't get themselves back into it and crashed out, losing 1-0.

Best: Chelsea 7-0 Ipswich Town (2011)

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After losing 3-1 to Chelsea in the FA Cup in 2009, the Tractor Boys returned to west London two seasons later for another bite of the cherry.

In 2011, however, the Championship side bit off more than they could chew.

This game was never a contest and Chelsea thrashed their lower-league opponents 7-0.

It was mesmerizing stuff at times, with Daniel Sturridge scoring two well-taken goals.

Roy Keane had lost his job as Ipswich Town manager days before the game, and with a performance like this from his former team, it's not hard to see why.

Garry Hayes is Bleacher Report's lead Chelsea correspondent. All quotes were obtained first-hand unless otherwise noted. Follow him on Twitter @garryhayes

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