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In Focus: The kings of the FA Cup's storied history
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Matthew Hill
Arsenal are the FA Cup's most successful side
Arsenal are the FA Cup's most successful side

The FA Cup fifth round brought more drama as eight teams booked their place in the quarter-finals of the latest edition of football’s oldest competition.

Though the early stages are more synonymous with lower league sides hunting out giant-killings, holding the trophy aloft at Wembley is an achievement every player and manager dream of.

Here, we take a closer look at the most successful sides and individuals in the tournament's history as the 152nd edition heads towards the business end.

Most successful team — Arsenal (14 wins)

Arsenal have been making all the headlines so far this season and it is the Gunners who have lifted English football’s leading domestic cup more times than anyone else.

It was not until 1930 that the North London outfit enjoyed their first success — beating Huddersfield 2-0 in front of over 92,000 fans at the national stadium.

That was to be the start of a glorious love affair with the competition, reigning supreme on 13 further occasions since with their most recent triumph coming in 2020.

Nine of those have occurred since 1993, meaning Arsenal have won over a quarter of the FA Cup tournaments contested across the last three decades.

Manchester United are two behind the Gunners on 12 titles and Erik ten Hag may view the competition as his next chance of silverware this season.

Most successful player — Ashley Cole (seven wins)

Ashley Cole has lifted the FA Cup on a record seven occasions
Ashley Cole has lifted the FA Cup on a record seven occasions

Fittingly, it is an ex-Arsenal star in Ashley Cole who tops the list for most FA Cups won by an individual player — though a fair share of his successes came with city rivals Chelsea.

Cole, who earned 107 caps for England, was part of a legendary Gunners side that won the competition three times in four years in 2002, 2003 and 2005.

The left-back would leave Arsenal under a cloud one year after that final success — joining the Blues in a controversial move that brought him silverware on an even grander scale.

Further wins in 2007, 2009, 2010 and 2012 in West London earned Cole an unrivalled spot in the competition’s history.

All three of the next players on the list are former team-mates of the ex-Three Lions defender, with John Terry, Petr Cech and Patrick Vieira all boasting five wins.

Most successful manager — Arsene Wenger (seven wins)

Arsenal's legendary boss Arsene Wenger is the FA Cup's best-performing manager
Arsenal's legendary boss Arsene Wenger is the FA Cup's best-performing manager

Carrying on the Arsenal theme, it should come as little surprise that legendary Gunners boss Arsene Wenger tops the managerial charts when it comes to FA Cup wins.

The highly-regarded tactician, who was in charge for an iconic 22-year spell, first guided his side to the trophy in 1998 before enjoying two further gluts of success later in his tenure.

He oversaw the aforementioned wins in 2002, 2003 and 2005, before repeating the trick over a decade on with 2014, 2015 and 2017 victories.

Wenger’s closest rival is former Aston Villa boss George Ramsey who won the competition six times at the Villans between 1887 and 1920, with the Frenchman’s old foe Alex Ferguson tasting success five times with United between 1990 and 2004. 

Most runner-up efforts — Manchester United, Everton and Chelsea (eight losing finals)

Liverpool's win last season saw Chelsea lose a third straight FA Cup final
Liverpool's win last season saw Chelsea lose a third straight FA Cup final

An honour that no club would be desperate to hold, the trio of United, Everton and Chelsea top the charts for finishing on the wrong side of the most FA Cup finals.

All three have come up short in the showpiece on no less than eight occasions, though the Red Devils can at least console themselves with the second-highest tally of 12 victories.

Everton have won the competition five times, though not since 1995, while Chelsea have eight successes — although the Blues’ recent history in finals has been a frustrating one.

Last season’s penalty shootout loss to Liverpool saw them fall at the final hurdle for the third year running, becoming the first team in the competition’s history to suffer such a streak.


FA CupArsenalChelseaManchester UnitedEverton
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