On March 4, 2006, Goodwillie became the youngest ever player to score an SPL goal when he came off the bench to score for United against Hibernian at Easter Road.
A product of the Dundee United youth system, Goodwillie initially joined the club from Stirling-based boys' club Carse Thistle, he was spotted whilst playing with the Scottish Youth FA Development Squads. He signed as a professional for Dundee United in March 2005, and made his debut for the first team just four months later in the final of the pre-season Discovery Cup tournament against Sheffield Wednesday. His first appearance in a major competitive fixture was against Rangers in December 2005, with his record-breaking goal following in his fifth outing, all having been as a substitute. Goodwillie signed a new contract in October 2006, extending his stay until the end of the 2009-10 season.
Goodwillie has represented Scotland at several youth international levels, and is currently a member of the national Under-19 squad, scoring a first half hat-trick in February 2007 against Bosnia-Herzegovina.
On 1 November 2007, Goodwillie joined Raith on a two-month loan, which was subsequently extended until the end of the season.
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