Factual error: John Candy is at the top of the Calgary Tower having lunch. In the background you see a building called Bankers Hall which is slightly higher than the Calgary tower, that's fine except this was the 1988 Olympics, that building wasn't completed until late 1990.
Factual error: Early 1990s cars are outside the Relax Inn hotel in Calgary.
Factual error: The modern flag (since 1991) of the Russian Federation is at the Olympic Park. In 1988, Russia was still part of the Soviet Union, which used a red flag with a yellow hammer and sickle.
Factual error: The flag of Sri Lanka is visible at Olympic Park. Sri Lanka has never competed in the Winter Olympics.
Answer: The events depicted in Cool Runnings of the improbable Jamaican bobsled team were actually quite accurate, according to this page http://www.factmonster.com/spot/02olcrunnings.html.