The fifth season of the American television comedy The Office premiered in the United States in the 2008–2009 television season on NBC on September 25, 2008 and concluded on May 14, 2009. It aired on Thursdays at 9:00 p.m. EDT. Consisting of 26 episodes, the fifth season continued the American adaptation of the British TV series of the same name as a mockumentary portraying the daily lives of office employees in the Scranton, Pennsylvania branch of the fictitious Dunder Mifflin Paper Company.

Formatted to work on iPods.