Of course he'll be pissed off if its not completed by the summer tour. But we're buying big players from big teams who are under no obligation to sell. You can get Lindelof from Benfica by splashing the cash because this is how they make money. Chelsea and Madrid aren't motivated in the same way and moves for Matic and Morata would seem contingent on both teams lining up their replacements.
Hopefully they'll be on the plane come Sunday but I don;t think it can be Woodward's fault if Chelsea and Madrid are playing hard ball.