Robbie Keane, 19, became the most expensive teenager in British football at the time, completing a £6million move from Wolves to Coventry on this day in 1999.
Keane quickly earned a reputation as one of the Premier League’s most feared strikers and went on to establish himself as one of the most successful goalscorers in league history.
The Sky Blues have splashed a record on Keane after netting 29 goals in two seasons for Wolves in the second tier of English football.
The Irishman’s price tag proved not to weigh heavily on his shoulders and he made an instant impact after scoring both goals in a 2-0 win over Derby at Highfield Road on his debut.
However, Keane’s stay at Coventry didn’t last long after he made an impressive start to life at the club, scoring 12 in 31 Inter Milan spent £13million to bring him to Italy.
The youngster failed to adapt to life in Serie A and after six appearances in six months, Keane joined Leeds on loan in December 2000.
Despite a period of short spells at several clubs, it was at Tottenham that he settled after moving to White Hart Lane in 2002.
The Republic of Ireland international scored 112 times for the club in two spells – either side of an uninteresting spell at Liverpool – he made 306 appearances and won the League Cup in 2008 .
He was sent for a short spell on loan to West Ham before packing his bags for good in 2011 to move to LA Galaxy.
Keane returned to England on loan at Aston Villa in 2012 and scored three more top-flight goals to finish his career with 126 to his name in the Premier League, placing him 16th on the league’s all-time goalscorers list.