In Skovdahl's first season at Aberdeen, the club finished bottom of the 1999–2000 Scottish Premier League, but Aberdeen avoided a potential relegation play-off due to Falkirk not meeting the SPL stadium requirements. Despite overseeing one of the poorest sides in Aberdeen's recent history in his first season in charge, Skovdahl proved popular with the fans. In that first year he brought in many foreign signings, with mixed success, and among his signings were Arild Stavrum, Hicham Zerouali, and Roberto Bisconti. The one highlight of Skovdahl's first season was that Aberdeen reached both the 2000 Scottish League Cup Final and the 2000 Scottish Cup Final, but they lost both finals to Celtic and Rangers respectively.