All told, Jeff, who joined City at the age of 10, went on to play more than 120 games for the Club and was a key part of Joe Royle’s fondly remembered squad which secured back-to-back promotions in 1999 and 2000.
However, not only did Jeff achieve a childhood dream in representing City with such distinction.
What helped make the midfielder’s time with the Club even more memorable was that for several years sharing alongside him in the roller-coaster ride of emotions at Maine Road in that era was Jeff’s older brother, Jim.
Reflecting back now on his past City adventures, Jeff admits it was a magical experience to form one half of a Blues brothers’ partnership alongside Jim who himself figured almost 40 times for the Club before moving on in 2001 to Wrexham.
“Playing with my brother was special full stop,” Whitley junior reflects.
“We used to play in Alexandra Park and we’d train there for hours and hours then we’d go home and then talk about what it might be like to play professional football and this and that.
“It’s something that when it came to it, where we were playing together me and him were talking about it, we'd laugh about it, saying ‘This is amazing’. And it was amazing because it doesn’t happen all the time.
“I know City have had a number of brothers who have played at the club but for me and our kid it was just brilliant, absolutely brilliant.”
A Northern Ireland international, Jeff eventually left City in 2003 and went to play for Sunderland and Cardiff City amongst other clubs, serving both with great distinction.
However, Jeff admits the chance to realise his childhood dream and represent Manchester City remains the pinnacle of his playing career.
“I’d been a ball boy at City, stood in the tunnels as a ball boy and watched all these players walk past you and you’re thinking one day you might get the opportunity to play on that grass at Maine Road," Jeff adds.
“I came through the system (at City), so for me to be able to put on the shirt, go out and play for the Club that you’ve grown up with was special.
“Especially when your family support the club and for them it’s a big, big deal.
“It was no different for me, it was a wonderful. I had a wonderful time at City.”
The undoubted highlight of Jeff’s City career were those successive promotion campaigns under Royle which first saw City defeat Gillingham on penalties in a pulsating shoot-out during our unforgettable 1999 Second Division play-off final at Wembley.
Twelve months later, Whitley junior and City secured our ticket back to the Premier League thanks to a thrilling 4-1 win at Blackburn on the final day of the 1999/2000 season.
The 20th anniversary of that remarkable afternoon at Ewood Park, which saw thousands of City fans decamp to east Lancashire, falls next month and Whitley admits being a part of twin promotion winning City squads was indescribable.
“That 1998/99 season was amazing, and we had a follow up on the next season after that as well,” Jeff recalls.
“I don’t think anyone would have thought we’d have won back-to-back promotions but again, a lot of it I put it down to the squad, the players that Joe brought in, and the back room staff as they were really fantastic.
“It was a club where you knew the ground staff, you knew the ladies that cleaned your kit… it was that kind of place and all of that helps.
“It’s an amazing Club and was an amazing Club to play for.”