Antonio Conte kicked off transfer deadline day knowing he needed to bring in a wing-back, a central midfielder to replace Nemanja Matic and a striker to make up for the loss of AWOL striker Diego Costa.
He achieved two of these objectives with Zappacosta signing for £23m from Torino and Drinkwater for £35m from Leicester.
Both deals came through late in the day with Chelsea officially announcing transfers had gone through for the pair after the window slammed shut at 11pm last night.
But Conte failed to bring in a striker with Fernando Llorente opting to join rivals Tottenham from Swansea despite holding talks with the Blues over a move earlier in the day.
This has been a recurring theme for the Italian boss, who has grown frustrated with the club’s hierarchy for failing to secure his top targets this summer.
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He has already failed to get deals over the line for Alex Oxlade-Chamberlain and Romelu Lukaku.
Oxlade-Chamberlain completed a £35m move to Liverpool after rejecting a move to Stamford Bridge.
The winger had his medical at St George’s Park while on international duty with England.
While, Lukaku – who looked destined to re-sign for Chelsea – was poached by Manchester United earlier in the season.
As a result he was forced to go for alternative targets with Zappacosta signing in place of Oxlade-Chamberlain and Alvaro Morata filling the hole that Lukaku was meant to fill.
But nothing could have prepared Chelsea for what happened in the final hours of the window last night.
A £35m fee with Everton was agreed upon for Barkley and he apparently turned up at their training ground in Cobham with his agent for his medical.
However, during his testing Barkley changed his mind and opted to return to Goodison Park in what proved to be a sensational U-turn.
Other reports say he never turned up to the medical, but it proved to be an incredible turn of events regardless.
And Everton’s majority shareholder Farhad Moshiri seemed to be left in a state of shock too.
“We heard from his agent that he changed his mind and wanted to reconsider his position during the January transfer window,” Moshiri told Sky Sports.
“Technically he will be with us because he is under contract for another year. It’s a big surprise but that is football.”
Away from the Barkley debacle, Chelsea had a bid rejected by Bayern Munich for right-back Rafinha.
And two players departed with Jordan Houghton and Fikayo Tomori joining Doncaster Rovers and Hull on season-long loans, respectively.