The 1999 FA Cup semi-final replay, the battle of the buffet at Old Trafford and Roy Keane offering Patrick Vieira out in the tunnel at Highbury are just three highlights that spring to mind.
But when it comes to transfer dealings between the two the rivalry gets no less intense with United holding the upper hand having shafted the Gunners on more than one occasion.
FRANK STAPLETON 1981
Some of his team-mates cruelly suggested that the former Republic of Ireland striker used to smile first thing in the morning to get it out of the way, but despite not suffering fools gladly, Frank Stapleton did actually have a dry sense of humour and did his talking on the pitch.
In 1979 he helped Arsenal beat United 3-2 in the FA Cup Final which hurt Frank in some ways because unknown to many, he was actually a United fan. By the end of the 1980-81 season, Stapleton’s relationship with Gunners boss Terry Neill had hit rock-bottom so what better way to piss off your employer than by letting your contract run down and head off to your boyhood heroes of a free transfer.
Whilst at Old Trafford, Stapleton picked up FA Cup winners medals in 1983 and 1985 and in between these, scored United’s third goal in a Cup Winners Cup tie as they overturned a 2-0 first-leg deficit against Barcelona in 1984, in what is regarded by many United fans as the greatest ever European night at the Theatre of Dreams.
CRISTIANO RONALDO 2003
Picture the scene; Arsenal boss Arsene Wenger has been alerted of a prodigious Portuguese talent playing in the youth team at Sporting Lisbon and invites the youngster to North London in 2002, to talk about the possibility of a permanent move to the club the following summer. His paymasters at Arsenal, however, are reluctant to shell out the reported 12 million quid Sporting are asking for his signature.
Fast forward to August 2003 and Sporting ask Manchester United to play a friendly to open their newly constructed Estadio Jose Alvalade in which a young Cristiano Ronaldo stars. United boss Sir Alex Ferguson has seen enough in 90 minutes and reportedly goes hurtling into the Sporting dressing room after the game, waving a cheque for £12.4M after faking the signature of CEO David Gill, citing the youngster as the “best player he has ever seen”.
Back in North London, Arsenal execs are pissing themselves at Fergie’s impulsive move forgetting that the Scot has form in this department, buying Eric Cantona from Leeds after demolishing three bottles of his own finest claret and deciding to call Tykes boss Howard Wilkinson for a laugh.
ROBIN VAN PERSIE 2012
After eight years at Arsenal, Dutch striker Robin van Persie had an FA Cup winner’s medal, a Champions League and League Cup runners-up gong but no league title medal. Fed up of carrying a team that was pleasing on the eye but ultimately useless at winning things, van Persie weighed up his options and looked at where he could get fast-tracked to stand on the winner’s podium in the Premier League.
Manchester United assistant coach Rene Meulensteen knew van Persie well and convinced his fellow countryman that a move to M16 would guarantee him a title-winning medal and to prove it, the club would let him have the number 20 jersey as he would be helping them to their 20th league success. On April 22 2013, a Van Persie hattrick secured that 20th title for his club and his first in the English top-flight – mission accomplished.
DANNY WELBECK 2014
When Louis van Gaal was given the keys to the Old Trafford kingdom in 2014, his first job was to find a new home for striker Danny Welbeck who despite having been at Old Trafford since 2008, had spent more time in rehabilitation than leading the forward-line. With Sir Alex now sat firmly in the director’s seat, he suggested to the Dutch tactician that he should call his old adversary Arsene Wenger, to see if he fancied taking the player off their hands; for a laugh like.
Imagine their surprise when the Gunners came back with a resounding yes, giving United 16 million in the process.
When asked at a press conference why he’d sold Welbeck to a direct rival, van Gaal towed the party line claiming; “Welbeck doesn’t have the record of Robin van Persie or Wayne Rooney. We let him go because of (Radamel) Falcao, but also to allow the youngsters to fit in. That is the policy. That is why I am here.”
Everyone inside Old Trafford knew the real reason was that the Glazers were fed up of paying top insurance premiums for a player who took the nickname “sick note” to a new level.
HENRIKH MKHITARYAN 2018
Hindsight is a wonderful thing but back in 2018 when Manchester United and Arsenal agreed to do a swap deal involving Armenian international Henrikh Mkhitaryan and Chilean Alexis Sanchez, it seemed as though the Red Devils had shafted the Gunners once again.
New United boss Jose Mourinho was reported to have told club chiefs that he didn’t want anyone in his dressing-room with an unpronounceable surname, so Mkhitaryan had to go no matter what the cost to the club.
When Arsenal announced that Arsene Wenger was stepping down as coach at the end of the 2017-18 campaign, Mourinho (with the full blessing of Fergie) decided to take the piss out of the Frenchman one final time by sending Mkhitaryan south without anyone’s blessing.
United would ultimately end up with egg on their faces with Sanchez picking up 400K-a-week to stay at home with his puppies before finally being sent to Inter last summer to play in Serie A along with the Armenian, who rocked up at Roma for the 2019-20 season.