Jamie Vardy to Arsenal
The most recent entry on the list, Arsenal’s failed pursuit of Jamie Vardy in the summer of 2016 left Gooners and Arsene Wenger feeling very deflated.
Having taken everybody and their own fans by surprise by concluding a deal for Granit Xhaka very quickly at the start of the window, Arsenal fans didn’t have to wait too long to then hear about Arsenal’s firm interest in Vardy.
Vardy was of course basking in the glory of just having won Leicester City their first ever Premier League title but this one really was a case of will he, won’t he with nobody being able to categorically claim his future whereabouts.
With Arsenal having met the England international’s release clause, the former Fleetwood Town striker then flew to Euro 2016 without giving Wenger the final word on the decision he had made.
It was a gruelling wait for Gooners who had to contend with masses of rumours before Vardy eventually came round to claiming it was an easy decision to remain at Leicester.
Didn’t seem that easy to all of us football fans however, given his stalling!