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Nineteen-year-old Robbie Keane became the then most expensive teenager in British football, completing a £6million move from Wolves to Coventry, on this day in 1999.
Keane had soon made a reputation as one of the most feared strikers in the Premier League and later cemented himself as one of the most successful goalscorers in the league’s history.
The Sky Blues splashed a record fee on Keane after he smashed in 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 he netted both goals in a 2-0 win over Derby at Highfield Road on his debut.
However, Keane’s stay at Coventry did not last long after he made an impressive start to life at the club, scoring 12 in 31, Inter Milan spent £13million to take 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.
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Despite a spell of short stays at several clubs, it was at Tottenham where he settled down after he switched to White Hart Lane in 2002.
The Republic of Ireland international scored 112 times for the club over two spells – either side of an uninspiring spell at Liverpool – he made 306 appearances, and won the League Cup in 2008.
He was sent for a short spell on loan at West Ham before he packed 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 end his career with 126 to his name in the Premier League, putting him 16th in the league’s all-time goalscorers list.