It took until five years into Wenger's reign at Arsenal for the pair to face each other for the first time
With a total of 26 meetings now behind them, there have been plenty of flashpoints along the way - but how has the dynamic between the two evolved?

The Bolton years

Allardyce undoubtedly enjoyed his greatest successes against Wenger's Arsenal during his seven and a half years in charge of Bolton.
It wasn't until after Wanderers won promotion to the Premier League in 2001 that the two crossed paths and the sides drew 1-1 in one of the Lancashire club's first games back in the top flight.
Arsenal would win their next two meetings but those successes stand as just four Wenger had in 12 games against Allardyce while he was resident at the former Reebok Stadium.
Allardyce enjoyed his best sequence of results against Wenger when he was in charge of Bolton Wanderers
Allardyce enjoyed his best sequence of results against Wenger when he was in charge of Bolton Wanderers
Even now, the Gunners manager concedes he still hurts from a 2-2 draw with Bolton in 2003 which went some way to costing his team the title that year.
Speaking as recently as December, he said: "I'm competitive and every disappointment stays with me for ever. It is a scar on your heart.

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"It is the problem of my life, basically. Unfortunately, you have awkward moments and you never forget them - but it is part of the game."
Allardyce was frank in his 2015 book, Big Sam, The Autobiography, about the satisfaction he took from depriving Wenger of positive results.

Allardyce's Bolton record v Arsenal

Date Result Winning Manager
22/09/01 Arsenal 1-1 Bolton Draw
29/04/02 Bolton 0-2 Arsenal Wenger
21/09/02 Arsenal 2-1 Bolton Wenger
26/04/03 Bolton 2-2 Arsenal Draw
20/12/03 Bolton 1-1 Arsenal Draw
20/03/04 Arsenal 2-1 Bolton Wenger
18/09/04 Arsenal 2-2 Bolton Draw
15/01/05 Bolton 1-0 Arsenal Allardyce
03/12/05 Bolton 2-0 Arsenal Allardyce
11/02/06 Arsenal 1-1 Bolton Draw
25/11/06 Bolton 3-1 Arsenal Allardyce
14/04/07 Arsenal 2-1 Bolton Wenger
He wrote: "I enjoyed beating Arsenal more than anyone when I was in charge at Bolton. We'd really got to them and Arsene Wenger hated us.
"We drew with them or beat them more often than expected and Wenger couldn't handle it. There was one time he wouldn't shake hands with me at Highbury because we got a draw.
"I saw him ripping his tie off and throwing it on the floor in anger. He takes it all very personally and has an air of arrogance."
We look ahead to the Monday Night Football clash between Crystal Palace and Arsenal
We look ahead to the Monday Night Football clash between Crystal Palace and Arsenal

Continuing to shock

Allardyce took his ability to rile Wenger with him when he left Bolton - firstly to Newcastle, where his sole game against Arsenal ended in a 1-1 draw.
Although results were heavily weighted in the London club's favour when Allardyce later went to Blackburn, he did inflict one defeat which had lasting ramifications.
Allardyce claimed in his 2015 autobiography Wenger had an 'air of arrogance'
Allardyce claimed in his 2015 autobiography Wenger had an 'air of arrogance'
Having been just two points off the top of the table with seven games to play in 2009/10, Arsenal proceeded to win just one of their next five league matches and fell out of contention.
The last place Wenger needed to go was Ewood Park, yet another setback came there as Allardyce's team won 2-1 and effectively rubbed salt in the visitors' wounds.
Wenger was unhappy with how the game was allowed to pan out, however, accusing Blackburn's players of targeting his goalkeeper Lukasz Fabianski at set pieces.

Allardyce v Arsenal at Newcastle and Blackburn

Date Result Winning Manager
05/12/07 Newcastle 1-1 Arsenal Draw
14/03/09 Arsenal 4-0 Blackburn Wenger
04/10/09 Arsenal 6-2 Blackburn Wenger
03/05/10 Blackburn 2-1 Arsenal Allardyce
28/08/10 Arsenal 2-1 Blackburn Wenger
He said: "Blackburn's main purpose every time was to stop the keeper. I cannot understand why he (referee Martin Atkinson) did not stop that.
"I do not know any more what is a foul and what is not a foul. Every time [a ball went in] Fabianski was pushed. There is no purpose to play the ball from the Blackburn players.
"They don't even watch the ball. He [Fabianski] had two players in front of him all the time and every time it was to stop him getting the ball."
Allardyce admits he loved beating Arsenal when he was with Bolton, something he did on three occasions
Allardyce admits he loved beating Arsenal when he was with Bolton, something he did on three occasions
The fall out ran for some time, with Allardyce issuing a pointed response before a rematch at the Emirates a little under four months later, which saw Arsenal win 2-1.
He said: "I have to remind Arsene about his team, which used to win the league, that was the dirtiest team in the league.
"If you cast your mind back to when they were winning the league, they had more sendings-off and bookings than anyone else.
"Arsene is almost, almost, affecting the officials so that you can't tackle an Arsenal player. That's something he's very clever at working on and it's almost working in his favour, you can see that.
Wenger was unhappy at how Lukasz Fabianski was singled out in Blackburn's win over Arsenal in May 2010
Wenger was unhappy at how Lukasz Fabianski was singled out in Blackburn's win over Arsenal in May 2010
"There is a perception that we kick everybody and Arsenal's motivation is that you can't tackle us as you aren't supposed to."

Wenger's best run

Going into Monday's game, Wenger is unbeaten in 10 meetings with Allardyce, a run which began with that 2-1 victory over Blackburn in the first weeks of the 2010/11 campaign.
When Allardyce went to West Ham, he won promotion back to the Premier League then enjoyed three mid-table finishes - yet his record against Arsenal nosedived spectacularly.
Wenger's side won each of their six games in that period - all bar one by at least two goals - and yet the Frenchman, somewhat curiously, remained critical of his opposite number's style.

Wenger's unbeaten run v Allardyce

Date Result Winning Manager
28/08/10 Arsenal 2-1 Blackburn Wenger
06/10/12 West Ham 1-3 Arsenal Wenger
23/01/13 Arsenal 5-1 West Ham Wenger
26/12/13 West Ham 1-3 Arsenal Wenger
15/04/14 Arsenal 3-1 West Ham Wenger
28/12/14 West Ham 1-2 Arsenal Wenger
14/03/15 Arsenal 3-0 West Ham Wenger
05/12/15 Arsenal 3-1 Sunderland Wenger
24/04/16 Sunderland 0-0 Arsenal Draw
01/01/17 Arsenal 2-0 Crystal Palace Wenger
With Jose Mourinho likening West Ham's tactics to "football from the 19th century", Allardyce continually found himself speaking out against the reputation he had for playing long-ball football.
He also cited Wenger as someone who used their approach as an excuse for his own team's performances against them.
Nevertheless, relations thawed over time, due perhaps in part to the fact Wenger was dominating whenever they came together.

Nowadays…

By the time Allardyce became England manager last year, he admitted Wenger was one of the managers he had to build bridges with to ensure players were released for international duty.
He said: "I would like to get round everybody and make some contact and hear their thoughts. We've got to try to help each other if we possibly can. It won't always be the case."
Wenger won all six of his matches against Allardyce's West Ham when the Englishman was in charge at Upton Park
Wenger won all six of his matches against Allardyce's West Ham when the Englishman was in charge at Upton Park
Allardyce's reign, of course, lasted just one game before he lost his job following the Daily Telegraph's investigation into corruption in football.
He was alleged to have offered advice on how to get around rules on player transfers.
Wenger said: "You have to let Sam Allardyce defend himself and I just hope he will clear his name. We have to be careful, we live in a society that is very quick to accuse people."
Allardyce admitted wishing to build bridges with Wenger after he was appointed as England manager last year
Allardyce admitted wishing to build bridges with Wenger after he was appointed as England manager last year
Allardyce was out of the game for three months before joining Palace and, in his second game, came up against Arsenal.
Predictably, it was Wenger who came out on top again - but only after he had showered praise on Allardyce in pre-match interviews.
He said: "He has the quality of a guy who is intelligent as he adapts to the level of his team and makes it simple for them to apply what he wants. I believe adaptability is one of his strengths."
Wenger supported Allardyce after allegations were made against him during an investigation by the Daily Telegraph
Wenger supported Allardyce after allegations were made against him during an investigation by the Daily Telegraph
Allardyce also insisted there was no longer any animosity between the two, instead launching an impassioned defence of a man who still remains under pressure at his club now.
He said: "Because of what Arsene did in the past, because he was that successful in his earlier days, they (fans) can't quite understand why they haven't been that successful again.
"It is much more difficult to do what his Invincibles team did in the current day but Arsene is certainly the man to build a football club.
"They've spent £500million on a stadium and he's still qualifying for the Champions League every year.
Allardyce maintains relations between him and Wenger are much better nowadays
Allardyce maintains relations between him and Wenger are much better nowadays
"I've had some good fun with Arsene. I got under his skin but those were the early days. Our meetings have been much more amicable since, on and off the field.
'I've always had a huge amount of respect for him. Winding-up was just a procedure we used as and when it was necessary."
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