Chelsea Advent: Five famous fives

On the fifth day of our advent calendar, we focus on the number five and some of the great players, goals and victories associated with it…

Arsenal 0-5 Chelsea 1998

The Blues ran riot at Highbury in November 1998, despatching our London rivals in the fourth round of the Worthington Cup. A Frank Leboeuf penalty set us on our way, before two goals apiece for player-manager Gianluca Vialli and Gustavo Poyet secured our then-biggest victory against Arsenal.

Chelsea 5-0 Manchester United 1999

Alex Ferguson’s Treble winners were put to the sword by a devastating attacking Chelsea performance at the Bridge. Poyet opened the scoring inside the first minute, and goal-shy Chris Sutton doubled our lead on the quarter-hour. After Nicky Butt was sent off, we asserted our authority in the second half with a further strike by Poyet, a Henning Berg own goal, and, the cherry on top of the cake, a late Jody Morris effort. It was some way to end the visitors’ 29-game unbeaten league run and earn our best victory against Man United.

Galatasaray 0-5 Chelsea 1999

A few weeks later, the Blues travelled to Istanbul – or ‘Hell’ as the local supporters brandished it – to play Galatasaray in the Champions League group stage. What followed was a remarkable European performance as we silenced the Ali Sami Yen stadium with two fine finishes from Tore Andre Flo and then one each for Gianfranco Zola, Dennis Wise and Gabriele Ambrosetti. A truly heavenly performance from Vialli’s men.

Chelsea 5-0 Everton 2016

Arguably the finest performance of our 2016/17 title-winning campaign, the Blues caught fire on Bonfire night with Eden Hazard leading the charge against a mesmerised Toffees. Our brilliant Belgian netted twice, Marcos Alonso scored his first in Blue and there were also goals for Spanish internationals Diego Costa and Pedro. The Toffees didn’t muster a shot on target.

Chelsea Women 5-0 Reading Women 2021

The Blues retained our WSL crown in style, with a final-day thrashing of Reading at Kingsmeadow. Melanie Leupolz got us up and running after just 68 seconds, with the brilliant Fran Kirby scoring either side of the interval to all but secure the title. Sam Kerr and Erin Cuthbert added the gloss late on as Emma Hayes’ side underlined their status as England’s best.

Frank Leboeuf (1996-2001) – Our silky French centre-back possessed a powerful penalty and a World Cup winners’ medal. 200 apps, 24 goals.

Michael Essien (2005-2014) – The all-action Ghanaian midfielder was central to two of our Premier League triumphs and was the scorer of that goal against Arsenal. 223 apps, 33 goals.

Gilly Flaherty (2014-2018) – A rock-solid centre-back, she played a key role in our first two WSL triumphs and has been inducted into the league's Hall of Fame. 96 apps, 11 goals.

Jorginho (2018-2023) – An ice-cool penalty taker, pass picker, and Champions League winner in 2021. 187 apps, 29 goals.

Sophie Ingle (2012/13, 2018-present) – The deep-lying midfielder has played more WSL games than anyone else, with the majority coming over two spells with Chelsea. 214 apps, 12 goals.

George Hilsdon v Glossop, September 1906 - Hilsdon made a spectacular start to his Chelsea career, scoring five times on his debut in a 9-2 win over Glossop North End. It was a performance that earned him the nickname 'Gatling Gun.'

Jimmy Greaves v Wolves, August 1958 – the first of a remarkable trio of five-goal blitzes for the Blues, this Greaves quintet more or less ended the career of iconic England defender Billy Wright. He may have only been 18, but Greaves was already too hot to handle, notching a remarkable 37 league goals despite the team’s struggles in 1958/59.

Bobby Tambling v Aston Villa, September 1966 – The featured game on that evening’s Match of the Day, viewers were treated to a Tambling masterclass. Our second all-time goalscorer netted a hat-trick before the break and twice more after it as the Blues made light work of our opponents at Villa Park, winning 6-2.

Peter Osgood v Jeunesse, September 1971 – It is no surprise that in our biggest-ever victory, the King of Stamford Bridge managed to find the net five times. Part-timers Jeunesse Hautcharage were blown away 13-0, with Ossie helping himself in front of goal, although having scored twice in the opening six minutes he might have hoped for more!

Gordon Durie v Walsall, February 1989 – Bobby Campbell’s Blues romped to the Second Division title with goals galore along the way. The biggest victory came at beleaguered Walsall, with Scottish striker Durie scoring five goals and laying on an assist for Kevin Wilson in a 7-0 success. It was some day out in the Midlands!

John Hollins was a complete midfield player who made almost 600 appearances for the club during two separate spells.

A youth team product, Hollins debuted aged 17 and played for us in the 1960s, 1970s and 1980s during an era of mixed fortunes for Chelsea.

He was central to our FA Cup win in 1970 and Cup Winners’ Cup triumph 12 months later, leading by example from the middle of the pitch.

In total, John scored 64 times in 592 appearances, and later spent two-and-a-half years as our manager. He passed away last year.