In recent years, Tottenham have had to be patient when it comes to the transfer window, but more often than not the fans’ faith in their club has paid off.
There have been some brilliant players to step through the doors in north London, and there are too many names to mention which deserve to go down in history for their talents.
However, as with every club, there are also those who will be remembered for all the wrong reasons, and while Spurs’ business in the transfer window has been pretty impressive in recent years, there is still the odd miss among the numerous hits pulled off by Daniel Levy and his team.
So just who are the very worst of the bunch?
Here, Football Insider picks out the five biggest flop signings since the Premier League began, including one man who is still on the club’s books, picking up a reported £25,000-a-week.
Click below to find out who sits fifth in our worst Tottenham signings in the Premier League