The Road to Guantánamo, alternatively The Road to Guantanamo, is a British 2006 docudrama film written and directed by Michael Winterbottom and Mat Whitecross about the incarceration of three British citizens (the 'Tipton Three'), who were captured in 2001 in Afghanistan and detained by the United States there and for more than two years at the detainment camp in Guantanamo Bay Naval Base, Cuba. It premiered at the Berlinale on 14 February 2006, and was first shown in the UK on Channel 4 on 9 March 2006. The following day it was the first film to be released simultaneously in cinemas, on DVD, and on the Internet.

The film was generally well received: Michael Winterbottom and Mat Whitecross won the Silver Bear for Best Director at the 56th Berlin International Film Festival, and the film won the Independent Spirit Award for Best Documentary Feature at the Sundance Film Festival. The Times criticised Winterbottom for accepting the men's stated reasons for going to Afghanistan at a time of danger after the 9/11 attacks in the United States, as it was known as al-Qaeda and Taliban territory.