Steve Sidwell was signed by Mourinho in June 2007 from Reading on a free but the central midfielder didn't even get a look in during his short time at Stamford Bridge. He only managed fifteen league appearances and failed to break into the first team, which is perhaps of little surprise when you consider he had the likes of Michael Ballack and John Obi Mikel ahead of him in the pecking order. Sidwell may have featured higher on this list had he not joined on a free but he still goes down as one of the more forgettable signings in the Mourinho era. He was sold to Aston Villa just one season after joining.