Robbie Keane's arrival at White Hart Lane was a long time coming. He was first supposed to arrive from Wolverhampton Wanderers, his first club, where Spurs lined up a move for him in 1999, but that never came to fruition. Instead, having scored 24 goals in 67 starts for Wolves, he moved across the Midlands to Coventry City, where he cost them £6 million.
The Sky Blues got a good deal, as Robbie was again in the headlines for scoring frequently, with two on his debut and 11 for the season in 31 matches. So impressive had he been in that first season at Highfield Road, that Internazionale of Milan came knocking and Coventry needing the money, took £13 million in return for the Irishman's services.
Having knocked around at struggling Inter for a few months without managing to establish a place in the side, Robbie chose to return to England with Leeds, where he made an immediate hit. Beginning the deal on loan and then signing a permanent transfer at the end of 2000-2001, he cost the Yorkshire club £12 million. His goals got the fans on-side, but manager David O'Leary preferred the pairing of Viduka and Alan Smith, leaving Keane out in the cold and benched for much of the season. He recovered to have a fantastic World Cup in Japan with the Republic of Ireland and that put his skills on display for potential suitors. With financial pressure closing in on his club, they had to sell players and Spurs cannily waited until the day of the August 2002 transfer window to make a deadline steal for £7 million.
Although he has moved around a fair bit since his entry into football, you know what you are getting with a player like Keano. Someone how is bright, never stops running and will always get you a goal out of nothing. His ability to score and provide goals is his strength, but he is also shrewd in knowing when the ball should be played and when to move into space. More than just a goal-scorer, he stayed with Tottenham during periods out of the side, but has been vice-captain for the team and looks set to be at White Hart Lane for the foreseeable future.
Scored his 100th goal for Tottenham against Sunderland at White Hart Lane, after coming on as a substitute, on 19th January 2008.
Despite signing a new extension to his contract to take him through to 2012, comments by Rafael Benitez on the club's website started a campaign to sign the player, having put the thought into his mind and a complaint to the FA by Tottenham ended up with it being withdrawn as the player was released to join Liverpool for £19 million (with an extra £1.3 million depending on conditions being met) and an apology about the tapping up and a donation to the Tottenham Hotspur Foundation by the Merseyside club on 28.07.08.
After a disappointing 189 days on Merseyside, during which he didn't seem to be wanted by the manager, rumours of his return to Tottenham were met by questions being answered in the media by Harry Redknapp and Rafa Benitez claiming that Spurs were "tapping up" their former striker. However, on transfer deadline day 2nd February 2009, the Irishman came back to White Hart Lane in a straight cash deal, rather than a swap for Aaron Lennon, as some sources hinted might be the case. In returning to Tottenham, he became the third most paid for player in football history at that time with transfer fees totalling £73 million.