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After a take-over battle with Robert Maxwell, Sugar teamed up with Terry Venables and bought Tottenham Hotspur football club in June 1991. Although Sugar's initial investment helped ease the financial troubles the club was suffering at the time, his treatment of Tottenham as a business venture and not a footballing one made him an unpopular figure among the Spurs fans. In Sugar's nine years as chairman, Tottenham Spurs did not finish in the top six in the league and won just one trophy, the 1999 Football League Cup.

Sugar sacked Venables the night before the 1993 FA Cup Final, a decision which led to Venables' appealing to the high courts for reinstatement. A legal battle for the club took place over the summer, which Sugar won. The decision to sack Venables angered many of Tottenham fans, and Sugar later said, "I felt as though I'd killed Bambi."

In 1992 he was the only representative of the then big five (Arsenal, Everton, Liverpool, Manchester United and Tottenham) who voted in favour of SKY's bid for Premier League television rights. The other four voted in favour of ITV's bid, as it had promised to show big five games more often. At the time of the vote, Sugar's company Amstrad was developing satellite dishes for SKY.

in 1998, and began the next season with just 3 points from their opening three games. Sugar next appointed George Graham, a former player and manager of bitter rivals Arsenal. Despite his earning Tottenham's first trophy in 8 years, the Spurs fans never warmed to Graham, partly because of his Arsenal connections. They disliked the negative, defensive style of football which he had Spurs playing; fans claimed it was not the "Tottenham way".

In February 2001, Sugar sold his majority stake at Tottenham to leisure group ENIC, selling 27% of the club for £22 million. In June 2007, Sugar sold his remaining shares to ENIC for £25 million, ending his 16 year association with the club. He has described his time at Tottenham as "a waste of my life".

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Q: What year did Lord Alan Sugar buy Tottenham Hotspur?
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