I'm not that much into space sims but I really loved X-Wing by the time when it came out and Tie Fighter was even better! Played those for hours and hours. I never got to play X-Wing vs Tie Fighter though.
The very first space sim I played and found kinda interesting was Skyfox II: The Cygnus Conflict on the C-64. According to MobyGames that was back in 1987.
Still no end: one of the first games I got and one I REALLY loved on the C-64 was Starglider, not really a space sim but almost.
