Bill Nicholson is, without a doubt, the biggest Tottenham Hotspur club legend of all time. The former player and manager had, in total, a 68 year association with the club - and no other clubs at all - including making 314 professional appearances for them in a seventeen year playing career as a wing-half between 1938 and 1955, scoring six goals. As a player, he won the league title with the club in 1951. More impressively, he managed the club for sixteen years between 1958 and 1974 in what was undoubtedly the most successful spell in the club's history. He won the league title in 1961, completing a league and cup double in that year, as well as two additional FA Cups in 1962 and 1967, the League Cup in 1971 and 1973, the European Cup Winners' Cup in 1963 and the UEFA Cup in 1972. He also took the club to the European Cup semi-finals in 1962 and was runner-up in a couple of other competitions in his time in charge. His most famous quote - often said to be one of the greatest managerial quotes of all time - was "It is better to fail aiming high than to succeed aiming low. And we of Spurs have set our sights very high, so high in fact that even failure will have in it an echo of glory." Nicholson passed away in 2004 at the age of 85 after a long fight with illness. It was one of the saddest days in Spurs' history, but he was widely celebrated - more than deservedly so - and his legacy will live on forever. He is in the English Football Hall of Fame and the road leading up to White Hart Lane is named Bill Nicholson Way. So there you have it - the ten darkest Spurs moments of the Premier League era. Did you enjoy this article? Do you agree with the entries on this list? Which other moments of Spurs' Premier League history have been particularly dark? Let us know your thoughts in the comments section below. And please feel free to follow me on Twitter!
