In 2008–09 season, Daly made his first appearance, coming on as substitute, in a 2–0 loss against Kilmarnock on 30 August 2008. Soon a week later, Daly scored two goals in consecutive games, against Hearts and Inverness Caledonian Thistle. He soon scored his first brace of his Dundee United career, in a 2–0 win against St Mirren on 29 November 2008, before scoring third goal in two consecutive games. Later in the season, his form dropped badly by coming on as a sub without scoring, often playing out of position, though making several starts. On 23 December 2008, Daly would sign a new three-year contract extension, that will keep him until 2012. On 11 January 2009, Daly provided assist for Prince Buaben before scoring a goal for himself, in a 4–0 win over East Stirlingshire, in the fourth round of Scottish Cup. In April 2009, Daly injured both his anterior and posterior cruciate ligaments, ruling him out of action for "at least 12 months", although he was later expected to return within half that timeframe. Shortly after suffering an injury, Conway scored a goal, in a 1–0 win over Hamilton, dedicating his goal to Daly.