Foremost amongst the pile of old games are a collection of Talensoft Battleground wargames. I bought these when I still had a computer that ran Windows 95 and haven't played them in years. I tried reloading one of the games on my laptop with its Vista OS and needless to say it didn't respond well. While this is a great pity its also an opportunity for me to get out and buy a more up to date version of the game.
Battleground Gettysburg (originally released in 1995) was my first purchase in the series and was one of my favorite games for a long time. I had a trial copy that I think came on a magazine CD and liked it so much I went out and bought the full version - the only time I've ever done this.
One scenario I played time and time again was Picketts Charge. I got slaughtered pretty much every time I played the Confederates but being a computer game I could go back to the beginning and try again, changing my strategy based on earlier games. I'd like to play this with miniatures one day, just to see if I learned anything from my virtual training ground.