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.
|Bills release Richie Incognito from reserve/retired list|
|Gentry and Pelicans want Cousins back in New Orleans|
|MLB extends Blue Jays closer Osuna´s administrative leave|
|Lloris, Jedinak and Kjaer ask FIFA to allow Guerrero to play at World Cup|
|Wolfsburg preserve Bundesliga status after play-off win over Kiel|
|Zidane was my idol and always will be - Wijnaldum|
|Liverpool ready to fly out of the blocks in Kiev - Henderson|
|Montreal Impact 0 LA Galaxy 1: Ibrahimovic sent off for slapping opponent|
|Real Madrid v Liverpool: Salah, Ronaldo lead the line in combined XI|
|Bertens keeps hat-trick hopes alive in Nuremberg|
|Monfils and Mannarino fail to fly the flag in Lyon|
|Morata, Fabregas, Herrera and more in Spain´s World Cup rejects XI|
|Reina to face FIGC hearing|
|Emery set to be appointed by Arsenal - reports|
|LeBron ´appreciative´ of hometown effort to put up statue of him|
|Cazorla leaves Arsenal after injury nightmare|
|Derby´s Rowett seeks permission for Stoke talks|
|Messi physically and mentally ready for the World Cup, Sampaoli proclaims|
|Murray expected to return at Rosmalen Grass Court Championships|
|More to Madrid than just Ronaldo - Robertson|
|Wolff: Red Bull and Ferrari favourites in Monaco|
|Iniesta hailed by Xavi as ´the most talented player in the history of Spain´|
|If you Googled ´European nights´, Liverpool would be top result - Klopp|
|Icardi cut from Argentina World Cup squad|
|Test recall a ´fantastic surprise´ for Buttler|
|Klopp needs Premier League to be a Liverpool great – Johnston|
|Salah is ´definitely´ world´s best - Lovren|
|Rhinos captain Watkins ruled out for eight months|
|No clue - Klopp defiant over Can to Juventus claims|
|Younis tips Babar for Pakistan greatness|
|Germany squad numbers hint at World Cup good news for Neuer|
|WATCH: Moto3 rider makes spectacular jump over crashed rival|
|Leaving out Morata ´painful´ for Spain boss Lopetegui|
|Gustard to leave England role for Harlequins|
|Nainggolan retires from Belgium duty after World Cup snub|
|Spain striker Morata misses out on World Cup selection|
|LeBron or Kawhi could lead Lakers to the Finals - World Peace|
|Serena steps up Roland Garros training ahead of French Open|
|Nainggolan left out of Belgium´s World Cup squad|
|The long goodbye: Iniesta sits alone in Camp Nou after final Barcelona match|
|Wane to leave Warriors at end of season|
|Dr Fury will see you now - Tyson plans future career in medicine|
|Harden, D´Antoni rue ´soft´ Rockets performance in Warriors drubbing|
|Liverpool players can change their lives in Kiev, says Gerrard|
|Real Madrid v Liverpool: Can great deeds of the past fuel the bid for Champions League glory?|
|Wash your mouth out! - Curry´s expletive outburst earns scolding from mother|
|Rakitic lost for words as Iniesta heads for Barcelona exit|
|Conte: Chelsea must overhaul squad to change style|
|Johnston: Liverpool can´t lose Suarez, Coutinho and Salah!|
|Messi: I like Griezmann, he´s one of the best|
|Ohtani says he´s not good enough for Home Run Derby yet|
|Mendy: France are eyeing World Cup glory|
|Scott accepts two-week ban for Walker punch|
|Braves rally for six runs in the ninth to defeat Marlins|
|MLS Review: Red Bulls upstage Atlanta thanks to Wright-Phillips brace|
|Warriors breeze past Rockets in game three|
|We have a quality squad – Man City chairman hints at caution in transfer market|
|Wise cruises to maiden PGA Tour victory at Byron Nelson|
|Matic: United can fight for Premier League and Champions League with experience|
|Golden Knights GM on Stanley Cup Finals berth: I don´t know how we did it|
|I did a ´s*** job´ defending LeBron James – Morris|
|Dembele suffers sprained right ankle|
|We know Fellaini´s not going to renew with United – Mirabelli suggests Milan move|
|Cavs´ Lue not satisfied with just one win|
|They even whistled at Torres – Simeone backs Griezmann|
|I arrived as a boy, I leave as a man – Iniesta in emotional Barcelona farewell|
|Lingard: Wembley loss my worst feeling in football|
|Cahill: Conte uncertainty affecting Chelsea|
|Sarri has run out of time – Napoli chief De Laurentiis|
|Barca boss Valverde salutes departing Iniesta|