A talented passer of the ball, Darren Caskey was lauded as one of the next big things, but unfortunately did not realise the potential he showed as a youngster.
A stocky midfielder, Darren had a good eye for a pass and also enjoyed getting into the opposition's penalty box to score goals, but his career did not take off the way he, and many others, hoped. An England international at a young age, he attended the FA School of Excellence at Lilleshall and captained the England Under-18 side to European Championship victory in 1993, leading by example and scoring the winning goal in a 2-1 win over Turkey in the final.
Caskey had signed with Spurs when he was 16 and progressed through the youth system to the point when he was given his debut as a 19 year old in a North London derby at White Hart Lane.
Was loaned out to Watford for a month in 1995 to give him the opportunity to get some first team action and when he returned, he was the better for it and starred in a match against Manchester United. His scurrying running style was complemented by a willingness to get stuck in when required and the vision to pick out team-mates in goals-scoring positions. But perhaps reliant on being allowed space to operate, Darren found opposition players in his face and this gave him little time on the ball, so he was often robbed of it or his passes were played hurriedly. The competition for a place in the Spurs midfield was hot, with Anderton, Dozzell, Fox and Dumitrescu all vying for places in the side. Without the drive to push his way into the team, he failed to show exactly what he was capable of.
Three years after his debut and forty odd games for Tottenham, Caskey was sold on to Reading for £700,000 and in a five year stay, played over 200 matches for the Royals and became well-liked in the Bedfordshire club. In 2001, he moved on to Notts. County, playing 100 plus times for the Magpies and being made captain and then on another free transfer, Darren signed for Bristol City. From there, short stops at AFC Hornchurch (leaving because of a financial collapse at the club), Peterborough United and Rushden & Diamonds followed, then a drop further down the leagues to play for Kettering Town (where he was player-coach), Halesowen Town and Ilkeston Town, where he is now a coach.