5 truly bizarre Transfer Deadline Day stories

#2 Benjani misses his flight and almost scuppers City move

Benjani missed two flights in an attempt to avoid a move from Portsmouth to Manchester City

Portsmouth’s Benjani was a man in form during the early part of the 2007-08 season, scoring 12 goals in 23 appearances for Pompey, and thus it came as no surprise when bigger clubs began to sniff around him as the January transfer window loomed. Once such side was Manchester City, and on deadline day, Portsmouth accepted an £8m bid from the Citizens for the Zimbabwean.

Bizarrely though, it didn’t seem that the striker himself was that interested in the move. Somehow, Benjani missed two flights from Southampton airport to Manchester, and when he managed to make it onto a third flight, he didn’t arrive at City’s training ground until 11:10 pm – leaving insufficient time to ink the deal before the midnight transfer deadline.

Naturally, neither side was too impressed with the incident, which the Zimbabwean blamed on tiredness – supposedly, he fell asleep in the airport – and Portsmouth, in particular, were left sweating as they’d used the funds from the Benjani sale to sign his replacement, Jermain Defoe.

Eventually, though, City were able to get their man, completing the deal a couple of days after deadline day with the Premier League approving their paperwork.

Nearly a decade on, Harry Redknapp – Pompey’s boss at the time of the move – recalled it as his most dramatic deadline day moment, suggesting he practically shoved Benjani onto the third flight, and that the stories of his tiredness were simply made up in an attempt by him to avoid the move altogether.