Born in Leicester, Weir-Daley started his career at Nottingham Forest in 1996 at 10 years old progressing through their Academy and making his debut after successful spells in the youth and reserve teams. He made his debut in a League Cup game against Macclesfield Town and scored on his Football League debut with Forest in a 3–1 away win over Gillingham. After eight first-team appearances, he was side-lined in November by a serious shoulder injury . That would keep him out for the remainder of the 2005–06 season.