At the start of the film, a subtitle announces "1959", indicating the year in which the story takes place. However the actual date of the last event of the film - Fidel Castro riding into Havana, marking the completion of the Revolution - was 1 January 1959. All of the preceding events must have occurred in 1958.
Dapes (Connery) examines General Bello's pistol and identifies it as a Beretta when in fact it is obviously a Colt M1911A1.
While Battista is watching a 16mm version of "Horror of Dracula" sequences are shown out of context. The scenes showing Christopher Lee's legs and hands disintegrating are shown prior to his hand-to-hand fight with Cushing.
A radio broadcast refers to Richie Ashburn as "former star center fielder for the Philadelphia Phillies". Ashburn did not leave the Phillies until after the 1959 season, at least nine months after the Cuban revolution.
When they cut to the Hotel Roma about forty five minutes in, the television said Channel 6, it should have said Chanel 6. It was filmed in Spain, and the movie was about Cuba.
The story is supposed to take place in 1959 but the limousine is a 1961 Chrysler.
Though the movie takes place at the end of 1958, the soundtrack includes the song "Pote Tin Kyriaki" -- "Never On Sunday" -- written for the 1960 movie of that name.