There was always going to be a risk appointing a former Arsenal manager as the boss at White Hart Lane and, despite his undeniable success at the Lilywhites' bitter North London rivals, that risk didn't really pay off. Graham took over from Christian Gross on the 24th of September 1998, after the strange Swiss coach had departed a couple of weeks earlier, and he lasted for nearly three seasons. He led them to an eleventh place finish in his first season, a tenth place finish in his second season, and was sacked in March of his third season after ENIC took over the club and accused him of breaching his contract by giving out private information. Graham did actually win the 1998-99 League Cup with Spurs, as a last minute Allan Nielsen goal gave his team a 1-0 win at Wembley against Leicester City, but his league performances ensure he finds a place on this list. All in all, Graham led Spurs in 97 Premier League games. He won 32 of them, drew 29 of them and lost 36 of them. His style of football was also very, very boring and not what Spurs fans expect from the team.
