I haven't owned a PC since the early to mid-90s so I am going to have to go old school on this and bear in mind the standards for a 'sim' were a lot less exacting back then:
Battle of Britain: Their Finest Hour
Aces Over Europe
Aces Over The Pacific
X-Wing
Tie Fighter
Most of those by todays standards would rank more in the arcady side of things, but back then just having red-outs in the Aces games was pretty amazing. Their Finest Hour came out waaaay back in 1991 and actually had sprites instead of polygons and ya know what? It was awesome, thats where I first learned how to do immelmans and split-s's. How do you realistically simulate an X-Wing? I think LucasArts did an amazing job trying and it was one of the best games I've ever played, def a top 5 ranker. If you've never played any of these get dos-box and give it a shot, you will have a blast.
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