At the 1988 Calgary Olympics, ski jumpers have their skis "v-style" (tips spread apart) while in the air. V-style ski jumping came to competition in the 1990s. At the Calgary Olympics, ski jumpers kept their skis parallel in the air.
In an early scene set in 1973, a train goes over a bridge which clearly has an electronic display board, something which wasn't introduced until at least 30 years later. It also strongly resembles a London underground tube S Stock train - something which is not operated in the north of England and wasn't introduced to London underground until 2011.
When Eddie's mum and dad are watching him on TV at Calgary 88, Eddie's dad want's to watch It's a Knockout on the other side. "It's a Knockout" was no longer on TV in the UK in 1988, the series finished in 1982, there had been a couple of episodes of _"Christmas Knockout" shown in 1983 and 1984 and _"Grand Knockout Tournament" ()_ which aired in 1987.
When Eddie is celebrating his first jump off the 70m at the Olympics, the frequently visible Finland flag that says "Flying Fin to win" is not the Finnish flag, as the cross of a correct Finnish flag is not centred. There are multiple Finnish flags throughout the movie that are correct, but this one is not. A more correct version of the Finnish flag can be clearly seen when Eddie's jump distance is being shown. In addition, a person who is from Finland is is a "Finn", with two n's.
During several of Eddie's jumps and most notably his final 90m attempt, the advertisement on the underside of Eddie's skis changes during the jump as the camera shot cuts back twice in a slow motion shot. The advertisement changes from "Fischer" to "fleuge.de", both of which are commonly seen on modern day jumping skis, not on skis of the time.
When the Calgary ski jump event is presented on television, Matti Nykänen is spelled correctly based on Scandinavian alphabets. In reality international competitions use AE instead of the actual letter Ä. Therefore Matti Nykänen was actually spelled in the international competitions as Matti Nykaenen. This has always been funny to Finnish people especially when there are more than one Scandinavian extension letter like the 80's cross-country skiing Olympic champion Marja-Liisa Hämäläinen who's last name was always spelled Haemaelaeinen before she got married.
The nose piece of the 1972 Pontiac Firebird that Bronson Peary works on has 4 scalloped headlight recessions, which first appeared on the 1979 model. This is consistent with the time line of the movie. The scene in question is set in winter 1987. Moreover this car make has been subject to car customizing regularly, so a '79 nose mounted on a '72 model is well possible.
In several scenes the Olympic logo only contains 4 rings instead of the official 5, this was actually used in the arenas at the actual games. Four rings were made to form the number '88, the year in which the Calgary games took place.
Establishing scenes during Eddie heading to Europe in 1987 have the Deacon Blue song REAL GONE KID playing over the top. Whilst it fit in with the mood of the scene quite nicely, this tune was not actually released until Autumn 1988. It doesn't really exist within the movie; it's for the audience's benefit.
The ski jump competitions Edwards took part in at the Calgary winter games were held on two February days, 01:30 resp. 02:00 PM local time. Given the time difference of 7 hours, in England it was around or even after sunset when it was Edwards' turn. Nevertheless in the movie, when his parents in England are watching him jump live on TV, bright sunlight is shining through the windows in the background.