Heartbreaking moments as a City fan - when your favorite player leaves

My 2 fav at the time left on the same day, Gary Owen and Peter Barnes, heartbroken at the time. As it turns out a big mistake aswell
 
For me, all players eventually leave but I think the thread is hinting at players who leave against their will or you feel still belonged at City. Hence, it was probably the right time for such as Sergio, Ilkay, Merlin and Zaba to leave.
Therefore for me, the choices are
Gary Owen
Georgi Kinkladze
Paul Stewart
Shaun Wright-Phillips
Tommy Caton
There are probably a few more but those are the ones that immediately come to mind
 
The whole Cole Palmer thread got me thinking.. is his exit even in my top 5 most heartbreaking losses of players moving on from City? And I would have to say no.. and I've only been a fan since 2010.

So in my opinion for me.. the top 5 most heart breaking exits were:

1. Gundogan
2. Tevez
3. Dzeko
4. Aguero
5. Jesus (just ahead of Sane)

What are your top 5 heartbreaking player exits as a City fan? Someone from the 70's, 80's, 90's, 00's??
Gabby ahead of dave , vinny or sane ? nah
 
Paul Stewart
Tommy Caton

As managers :-
Joe Royle (the back to back promotions were amazing but it meant he had players he bought to get us out of, what's now league one, trying to keep us in the prem). I though him leaving was harsh

At the time I was gutted when Keagan left (although i niw understand why). He had us playing some great football in the promotion season.
 

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