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.
|We all know where our nipples are - Hansen welcomes tackle trial|
|Rooney would thrive in MLS, says DC United boss|
|Pakistan complete demolition of sorry England|
|Curry, Durant reveal the secret to Thompson´s success|
|Salah will miss World Cup, claims Saudi sports administrator|
|Deschamps marvels at Zidane´s incredible Champions League success|
|FIA satisfied Ferrari ´inside the rules´|
|NSW Origin hopeful Moylan pulls the strings for rampant Sharks|
|Champions League blunders will stay with Karius - Clemence|
|Warriors assuming Iguodala won´t play game seven, Kerr says|
|Lampard confirms Derby talks over vacant managerial position|
|French Open 2018: The science behind Nadal´s clay-court dominance explained|
|Walsh to continue as Bangladesh head coach|
|Bale makes emphatic point after Champions League omission|
|Casemiro: I bet Ronaldo stays at Madrid|
|Brewers pull away for blowout win over Mets|
|Warriors´ outburst sinks Rockets, forces game seven|
|MLS Review: Timbers win sixth straight, Techera scores hat-trick|
|It was like wrestling – Klopp unhappy with Ramos challenge on Salah|
|McKinnon says 49ers aiming to win Super Bowl this season|
|Choo makes history with walk-off home run, Rangers seeking ball|
|Shin-Soo Choo makes history with walk-off home run, Rangers seeking ball|
|Marcelo: I think Cristiano Ronaldo will stay at Real Madrid|
|Miller-Uibo shines as Semenya sets record in Eugene|
|Rose extends lead as Spieth slides|
|Prompt recovery, Salah – Ramos wishes Liverpool star well|
|Indians reliever Miller headed back to disabled list|
|Warriors´ Iguodala to miss game six against Rockets|
|I shouldn´t have done it – Ronaldo accepts future comments mistimed|
|Klopp: Liverpool behind Karius after Champions League horror show|
|Karius´ final blunders could destroy his career – Kahn|
|Zidane understands Bale frustration|
|Bale, Karius send Twitter into overdrive in action-packed Champions League final|
|Ronaldo: It should be called the CR7 Champions League|
|Zidane revels in Madrid´s third successive Champions League title|
|I lost Liverpool the game – Karius apologises for Champions League errors|
|Barcelona congratulate Champions League winners Real Madrid|
|Salah injury update: Egyptian FA calm World Cup fears|
|Ronaldo must stay with Madrid - Zidane|
|Champions League final player ratings: Bale stars as Karius shocker costs Liverpool|
|Cristiano is happy and will continue to be happy – Perez cools Ronaldo future talk|
|Win as a team, lose as a team - Liverpool captain Henderson not blaming Karius|
|Modric: Madrid have built dynasty like Bulls, Celtics and Lakers|
|Where would Cristiano go? - Benzema predicts Ronaldo stays at Madrid|
|We do not think about that - Zidane shrugs off Ronaldo exit talk|
|The divine right of kings: Zidane´s Real Madrid ride luck all the way to greatness|
|Klopp fears Salah will miss World Cup|
|Du Plessis returns, 17 uncapped players selected by South Africa|
|Bale demands playing time after Champions League heroics|
|Ramos: Ronaldo is indispensable to Real Madrid|
|It´s been beautiful to play for Real Madrid - Ronaldo hints at shock exit|
|Salah injury marked beginning of the end for Liverpool|
|Bale double makes Champions League history|
|Bale, Mandzukic & the best Champions League final goals|
|Real Madrid 3 Liverpool 1: Brilliant Bale undoes Klopp and calamity Karius|
|Jokanovic proud Fulham stuck to style in Wembley win|
|Real Madrid´s Carvajal limps out of final to prompt Spain fears|
|Broughton and Catalans continue fine form|
|Tearful Salah off injured in Champions League final|
|Leinster complete historic double by beating Scarlets|
|Lions snatch win from Stormers, Brumbies stun Bulls|
|Bale sits out warm-up ahead of Champions League final|
|Cavaliers´ Kevin Love ruled out of game seven|
|Pavlyuchenkova saves two match points to win Strasbourg epic|
|Benzema comparisons have made me stronger, says Giroud|
|Pakistan´s victory charge frustrated by Buttler and Bess|
|Aston Villa 0 Fulham 1: Cairney secures Premier League return|
|Isco preferred to Bale in Champions League final|
|Castres hold off Racing to book Top 14 final berth|
|McIlroy recovers late to share Wentworth lead with Molinari|