After seven magnificent seasons at the Etihad, the German midfielder is moving on to undertake a new challenge at Barcelona.
Fittingly, the 32-year-old bowed out on the ultimate high, captaining City to Champions League glory against Inter earlier this month in Istanbul, a victory which saw the Club seal a historic Treble.
Watch Gundogan lift the Champions League trophy
That capped a magnificent period at City which saw Gundogan help the Club win 14 major honours in all, including five Premier Leagues, two FA Cups, four Leagues Cups and the Champions League.
However, just as significantly in Winter’s eyes alongside that stockpiling of silverware has been Gundogan’s enormous impact at the Club - both as a driving force at the heart of our midfield as well as the class and character which personifies the man and player.
“He’s brought intelligence, he has brought composure, and he’s brought dignity to City and to English football,” Winter reflected.
“There has been a class about him. You can just imagine him turning up at training in the morning and being instantly polite with everyone he comes across.
“Something like that is a sign of respect to all the people you work with.
“He has represented himself and the Club in a fantastic way.
“I don’t know him personally but my colleagues who have interviewed him, to a person, all say what an intelligent, likeable individual he is.
“Intelligent in that German way of having grown up and in their education system the German players tend not to leave early like many youngsters tend to do over here.
“I’m not sure if he went on to do his Abitur - but he certainly strikes me as every eloquent and so intelligent.
“And I can’t imagine there would be too many fans of other clubs who would have a bad word to say about him.
“He doesn’t dive, he doesn’t moan, and he has always communicated with officials in a civilised way and he has delivered in the biggest moments.
Watch Gundogan’s FA Cup final brace
“I would have loved to have seen him win a PFA award as a sign of the enormous respect which with he has been held in this country.”
Gundogan carried the distinction of being Pep Guardiola’s first signing after the Catalan had arrived to take charge at City in the summer of 2016.
He has since proved to be a pivotal figure in the way Pep’s City have not only gone on to dominate English football but also changed the way the game is played and thought about on these shores and beyond.
And for Winter, the German has to be in the conversation when it comes to a discussion about Pep’s best-ever signings.
“You could write a book on Pep’s key individual signings and Ilkay has got to be up there,” Winter continued.
“The joy of Pep is that not only does he sign well but he makes good players even better. You just see the players.
“Is he Pep’s best signing – that’s a tough one. But I would say as a leader, as an influencer on the pitch, as someone who scores goals in the biggest moments of the season, he’s absolutely got to be up there with Pep’s finest signings.
“He just seems to be ready for the big moments and he always sets the tone for everyone.
“He seems to say these are the moments that we are going to be judged on and the moments memories are made, and legacies are built and that’s when he stands tallest.”
