In 1996, Liverpool accepted offers from Leeds United and Tottenham Hotspur for Scales, who decided to again join up with "Spurs" manager Gerry Francis who he had played for whilst at Bristol Rovers. Scales had a disappointing time at Tottenham Hotspur due to injuries, being in and out of the team and the instability of the club. He scored once during his time at Tottenham with his goal coming, coincidentally, against former club Liverpool in the 1998–99 Football League Cup, which Tottenham went on to win. However, he missed the 1999 Football League Cup Final with a calf injury that he picked up in February 1999.