Mido (2007)
Back when City went over four months without scoring a home goal in the Premier League, manager Stuart Pearce hoped Tottenham striker Mido would prove to be the solution.
A £4m fee was agreed for the Egyptian, only for Spurs boss Martin Jol to call it off at the last minute.
"The doctor was there waiting to do a medical which tells you how advanced we thought it was," said Pearce.
"Then we get a call at 2330 GMT saying Spurs were pulling out. It was a bit of a bolt from the blue, that's for sure."
Mido eventually moved on to Middlesbrough and ended his career at Barnsley.
Kaka (2009)
It would be easier to just populate Kaka's entry with quotes from Garry Cook but some background is required.
After the Abu Dhabi United Group completed their takeover of City four months earlier, The Blues bid for David Villa, Dimitar Berbatov and Robinho on deadline day. They got the latter and they wanted another Brazilian.
Fast-forward to January and City were confident of signing 2007 Ballon d'Or winner Kaka for a world record £100m. Fans posed with a cardboard cut-out of the World Cup winner in a City shirt outside the Etihad. Another Blue got "Kaka" tattooed on his chest.
He never arrived, though, and joined Real Madrid in the summer. Over to City's then-chief executive Cook.
"If you want my personal opinion they bottled it," Cook said.
"He clearly was for sale but we never got to meet with the player, the behaviour of AC Milan got in the way."
Back then, it was a very different "Typical City".
Fernando and Eliaquim Mangala
The Porto pair eventually joined City in the summer, however The Blues were keen on tying up a double deal last January.
A private jet had been scheduled to arrive at the Manchester Airport's private terminal on deadline day and air traffic control records showed the plane was expected at 3.23pm.
However, it was removed from the system and City won two trophies without them.
Click below for our survey on City's January transfer window activity:
