The former Arsenal and England midfielder arrived at Maine Road via a short stay with Leeds United when David White moved to Elland Road in December 1993.
Rocastle moved to City in a straight swap valued at £2m and he made his debut against Blackburn in a 1-1 draw just before the New Year.
He was an instant hit with the fans and his class shone through immediately in a side that included a number of budget signings.
In fact, it was a City side seemingly headed for relegation, though that threat would not become reality for another couple of seasons.
Rocastle – or ‘Rocky’ as he was known to the football world - was a two-time league champion with Arsenal and represented a beacon of hope in a largely miserable period for City fans.
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The football wasn’t great, Peter Reid had been sacked at the start of the campaign and new manager Brian Horton was desperate to bring in some fresh players.
Reid had few flair players in his squad and his predecessor Howard Kendall had even fewer, so to have a player who could lift you out of your seat with a bit of magic every now and then made Rocky an instant crowd favourite.
For some reason, it felt like his stay would be a brief one and even though he was only 26, he had suffered numerous injuries in recent seasons and they were beginning to take their toll.
But Rocky still had what it took to thrill the City fans and, against Ipswich Town, he produced one moment of Brazilian skill that set up a goal for Carl Griffiths and all but lifted the roof off Maine Road.
It was a dummy, feign and drag back that saw him spin away from three defenders before his low cross was turned in by Griffiths at the near post to make it 1-1 which left the Kippax roaring “Oh, Rocky, Rocky! Rocky, Rocky, Rocky Rocastle!”
He continued to ooze class, even when he was having an off-day and the oft-heard comment around Maine Road was “Imagine if we’d have got him five years ago.”
Rocky only played 23 games for City and it’s amazing he made the impact he did given that he was only with the club for eight months – but he had and there was a great deal of disappointment when he was allowed to join Chelsea a few weeks before the 1994/95 season.
Though his career hadn’t flourished since leaving his beloved Gunners, Rocky's time with the Blues proved that, on his day, he was still one of the best English midfielders of his generation.
Things didn’t work out for him at Chelsea and he went on loan to Norwich and Hull while at Stamford Bridge.
He even tried his hand in Malaysia, but it wasn’t the swansong his career deserved.
Then, in February 2001, it was announced that he was suffering from non-Hodgkin’s lymphoma and just two months later, he passed away aged only 33.
Rocky left behind a wife and three children and though his time as a City player was short, he’d left a lasting impression on the pitch, and off it, where he proved equally popular.
He remains much missed by those who knew and loved him – or were lucky enough to see him play.
And as #RememberingRocky trends around the UK on this, the anniversary of his passing, we too remember Rocky.