And now, the end is near. Arsene Wenger certainly did it his way at Arsenal, but his reign at the club is drawing to a close.
The Frenchman caught the footballing world by surprise on Friday by announcing he will leave the Gunners at the end of the season, ending his 22-year tenure.
During over two decades in charge, Wenger has won the Premier League three times and lifted the FA Cup on seven occasions.
However, it hasn't always been plain sailing during his time in England. There have been near misses, painful departures and disappointing defeats.
Here, we recall five moments Wenger would probably like to forget (and that is without even mentioning his shoving match with Jose Mourinho in 2014).
THE END OF THE INVINCIBLES
Arsenal's Invincibles were unbeaten in the Premier League since May 2003 when they turned up at Old Trafford on October 24, 2004. However, after 49 games, the run came to an end in controversial circumstances.
Manchester United broke the deadlock when Ruud van Nistelrooy converted a contentious penalty awarded in the 73rd minute for a foul by Sol Campbell on Wayne Rooney, who later scored his side's second goal on his 19th birthday to wrap up a 2-0 win.
The final whistle saw the end of the action on the pitch, only for the bad blood to continue in the tunnel. There was no swapping of shirts and Campbell refused to shake Rooney's hand, despite the pair being team-mates with England.
Wenger reportedly confronted Van Nistelrooy before rival manager Alex Ferguson became involved, leading to what the media dubbed as "The Battle of the Buffet". Food was thrown in the direction of the United boss, who was forced to change before undertaking his post-match interviews.
HEARTBREAK IN PARIS
While he led Arsenal to glory domestically, Wenger has never quite managed to conquer Europe during his long time at the helm of the Gunners, although he may still bow out with Europa League success.
The closest they came to winning the Champions League was in the 2005-2006 season, as they knocked out Real Madrid, Juventus and Villarreal to set up a showdown with Barcelona in Paris.
Despite goalkeeper Jens Lehmann's early red card for bringing down Samuel Eto'o outside the penalty area, defender Campbell headed Arsenal into a 37th-minute lead.
Yet Wenger's men wasted several chances to double their lead, allowing Barcelona to rally in the closing stages. Eto'o levelled the game before Juliano Belletti grabbed the winner with 10 minutes remaining, beating replacement keeper Manuel Almunia at the near post.
86 - Arsene Wenger has won the most Champions League matches (86 - excluding qualifiers) without having ever won the competition. Frustration. pic.twitter.com/UIRbcF1CEE— OptaJoe (@OptaJoe) April 20, 2018
THE DEPARTING STARS
Just three months after losing the Champions League final, Wenger was dealt a further blow when one of his key players left in acrimonious fashion.
Ashley Cole's long relationship with the club came to a bitter end in August 2006. The divorce was particularly messy, with the left-back making the short move to London rivals Chelsea.
Less than a year later, Thierry Henry was gone too. After an injury-hit 2006-07 season, the club's record scorer joined Barcelona, the team that had denied Henry and Wenger in the French capital.
Both Cole and Henry went on to win the Champions League with their new clubs too.
AN OLD TRAFFORD NIGHTMARE
Manchester United 8 (yes, eight) Arsenal 2. At a ground where the Gunners had clinched the title in 2002, Wenger suffered one of his greatest football humiliations in August 2011.
With his team shorn of several first-team regulars due to injuries and suspensions, the Arsenal manager watched on as his patched-up side were torn to shreds by their long-time rivals.
Rooney led the way with a hat-trick and Ashley Young scored twice, while Danny Welbeck, Nani and Park Ji-sung also found the net, as Arsenal suffered their worst defeat since 1896.
To rub salt in the wound, Robin van Persie missed a first-half penalty against the club he would later join, while full-back Carl Jenkinson was shown a red card in the second half.
823 - Arsene Wenger has managed more Premier League games than any other manager (823) and only Sir Alex Ferguson has won more games (528) than Wenger (473). Longevity. pic.twitter.com/ktdsaZPb1y— OptaJoe (@OptaJoe) April 20, 2018
CITY SLICKERS INFLICT WEMBLEY WOE
Wenger has enjoyed plenty of success at Wembley, lifting the FA Cup at the famous stadium on several occasions, including the 2017 showpiece when Arsenal denied Chelsea from completing the double.
However, the League Cup has not been so kind for the former Grampus Eight boss.
Having lost the 2007 final against Chelsea in Cardiff, he suffered Wembley disappointment four years later when Obafemi Martins came off the bench to clinch unfancied Birmingham City the trophy at Arsenal's expense.
Yet this season's final loss to Manchester City was perhaps even tougher to stomach. While Pep Guardiola clinched his first trophy with the Citizens in style with a resounding 3-0 triumph, Wenger once again faced questions over his Arsenal future after failing to secure the one domestic honour that eluded him.
|Reported Liverpool target Dabbur to undergo Sevilla medical|
|Lebanon v North Korea: Radulovic calls on players to make history|
|MLS MVP Martinez signs five-year contract with Atlanta|
|WBC set deadline for Wilder-Fury rematch|
|Iran 0 Iraq 0: Team Melli top Group D after dull draw|
|Vietnam 2 Yemen 0: Quang Hai shines to give Golden Dragons hope|
|Bielsa admits to spying on all Leeds´ opponents|
|Valverde open to arrivals amid De Jong tug-of-war|
|Sexton named in Ireland squad for Six Nations openers|
|Higuain benched for Supercoppa Italiana amid Chelsea links|
|De Grandhomme, Latham and Santner back in Black Caps squad|
|Oman v Turkmenistan: Verbeek tells players to ´score as many as possible´|
|Japan v Uzbekistan: Cuper not distracted by potential last-16 opponents|
|Brown desperate for England recall|
|Lowry ties course record in Abu Dhabi|
|James is playing for Bayern future – Kovac|
|Wizards can compete for playoffs in LeBron-less East despite injuries - Brooks|
|Kyrgyzstan 3 Philippines 1: Lux hat-trick gives White Falcons third-place hope|
|South Korea 2 China 0: Son sets the standard as Bento´s men take top spot|
|Saudi Arabia v Qatar: Top spot on the line in Group E|
|Wasps pull off Fekitoa coup|
|Fresh injury woe for Real Madrid defender Vallejo|
|Home sweet home for Wozniacki as Stephens conquers Melbourne demons|
|Nadal: Victory over Ebden a step forward|
|Proteas rest Steyn and De Kock for opening ODIs|
|Nadal and Federer march on as rising stars prosper|
|Barcelona president Bartomeu convinced Valverde will stay|
|Inter forward Keita suffers thigh injury|
|Nadal races into third round with easy Ebden win|
|Kimmich ´perfect´ for Barcelona, says Xavi|
|Richardson and Nabi inspire Renegades´ rout of Sixers|
|This Liverpool isn´t a team of chokers – Mane|
|Central Coast Mariners 2 Melbourne City 1: Late Simon winner ends 10-match losing streak|
|Bryan backs Murray to return after hip resurfacing surgery|
|Scotland coach Townsend turns to trio of uncapped hookers|
|Spurs´ Aurier arrested on suspicion of assault, released without charge|
|That was a fireworks show - Warriors revel in record-breaking first quarter|
|We are in talks with Chelsea – Salihamidzic reiterates interest in Hudson-Odoi|
|´Proud´ Messi recognises impact of team-mates after reaching 400 LaLiga goals|
|Henry v Vieira: The Arsene Wenger proteges to move into coaching|
|Federer enjoys ´cat and mouse´ win over Evans|
|Wozniacki cruises through in Melbourne|
|Federer maintains perfect Australian Open second-round record|
|Warriors set NBA record, Butler´s 76ers rout Timberwolves|
|´I like the fact we beat them´ - 76ers´ Butler revels in win over Timberwolves|
|Murray says he´ll ´probably´ have operation|
|Australian Open tribute for Andy Murray surprises brother Jamie|
|Warriors score NBA record 51 points in first quarter against Nuggets|
|Panthers owner Tepper doesn´t rule out Newton missing 2019 because of shoulder injury|
|De Ligt will be world´s best centre-back – Koeman|
|Ronaldo a ´perfect machine´, says Gattuso|
|Barcelona? I can´t say anything - Stuani|
|Silva upbeat about Man City title chances|
|Celtics youngsters say Irving´s callout ´came from a good place´|
|NFL playoffs: Patrick Mahomes v Tom Brady|
|NFL playoffs: Jared Goff v Drew Brees|
|Sixers sign Brewer to 10-day contract|
|Lozano and Morgan scoop CONCACAF awards|
|Lakers ´optimistic´ about LeBron injury|
|Giants produce mammoth fourth quarter against Nymburk|
|Austin FC to join MLS in 2021|
|Henry, Vieira look forward to reunion when Monaco host Nice|
|Barcelona reject Neymar phone call reports|
|Wentz is the quarterback ´going forward´, says Eagles coach Pederson|
|Gattuso: Higuain has not asked to leave|
|Drew Brees by the Opta numbers: 10 facts for QB´s milestone birthday|
|Harry Kane injury: England captain´s history of ankle woe|
|Harry Kane injury: Opta numbers suggest Spurs struggles|
|Harry Kane injury: Tottenham´s options in striker´s absence|
|Allegri: Supercoppa clash practice for Champions League knockouts|