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Negredo and Richards depart City
Manchester City have offloaded striker Alvaro Negredo and defender Micah Richards to Valencia and Fiorentina respectively.
Both players have moved on a one-year loan deal.
Valencia announced the Negredo coup shortly after the 11pm deadline passed. The Spanish club will have the option to buy for £24 million in 12 months time.
Earlier on Monday, Richards, who is surplus to requirements at the Etihad Stadium, was pictured arriving at Florence airport as he prepared to seal a move to the Serie A club.
City had hoped to sell the 26-year-old, who has a year left on his contract, but had to accept a season-long loan deal for a reported £3.5m loan fee.
On their official website, City said: "Micah's last game for City was as skipper during the FA Community Shield defeat to Arsenal, and everyone at MCFC wishes him the very best for the coming campaign."
Richards is City's longest serving player and, after making his debut for them in 2005, appeared 255 times for his only club.
However, he struggled with injuries in the last two seasons - when Pablo Zabaleta established himself as City's first-choice right-back - and started only seven league games in 2012-13 and two in 2013-14.
The summer arrival of Bacary Sagna from Arsenal gave manager Manuel Pellegrini an alternative to Zabaleta and signalled the end of Richards' City career.
Pellegrini said in his news conference on Friday that Richards, along with winger Scott Sinclair and striker John Guidetti, was being made available to other clubs before the end of the transfer window.
He joins a series of English players who have left the Etihad Stadium this summer, with Joleon Lescott moving to West Bromwich Albion, Gareth Barry signing for Everton and Jack Rodwell joining Sunderland.