The timeline was screwed up long before Rocky V. For example, in part IV, Rocky and Adrian's 9th year wedding anniversary indicates it's taking place in present day (1985) because they got married a short while after his first fight with Apollo on 01/01/1976, but Apollo being retired for "nearly 5 years" indicates it's taking place in 1981 (Apollo retired after his second fight with Rocky on 11/25/1976).
It seems that Stallone kept getting confused between the time frame that the movies were supposed to be set in and the time frame in which the movies were made. For another example, Rocky II takes place in 1976 but it was made in 1979, so when Rocky III comes along, seemingly set in present day (1982), Rocky has been the champion / Apollo is said to have been retired for 3 years, though it should have been 6 years, i.e., the same age as their kid, who was clearly 6 or 7 years old (and indeed was played by an actor who was 7 years old at the time and in no way could have passed for a 3-year-old).
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