Dida was among a clog of goalkeepers on the Milan roster at the start of the 2008–09 season that included Kalac, Christian Abbiati, and 2007 signing Marco Storari. He was ultimately named second choice behind Abbiati, with Kalac demoted to third choice after conceding five goals in Milan's Russian Railways Cup loss to Chelsea on 3 August, and Storari being loaned to Fiorentina. Dida was designated to Milan's UEFA Cup campaign, in which he kept only one clean sheet in six matches as the "Rossoneri" were eliminated by eventual finalists Werder Bremen. On 15 March 2009, Dida played his first Serie A match in over a year after Abbiati suffered a season-ending knee injury during Milan's 5–1 win at Siena. He finished the season as starter, keeping six clean sheets in a career-low ten league appearances as Milan placed third behind Inter and Juventus and returned to the Champions League.