Billingsley also started 3 postseason games for the Dodgers in 2008. In his first postseason appearance, Billingsley pitched a strong innings, while allowing just one run against the Chicago Cubs. The Dodgers won the game 10–3. However, in his next two starts, Billingsley was not nearly as effective. Lasting only innings, Billingsley was torched for 8 runs (7 earned) in an 8–5 loss to the Philadelphia Phillies in Game 2 and innings, while giving up 3 earned runs, in Game 5 of the 2008 NLCS. He received some criticism for not brushing back (i.e., pitching far inside) to Phillies batters when Dodgers hitters were knocked down several times.