Defender of The Crown - Heroes Live Forever. The original DotC requires DosBox, so I opt for the (a bit fresher) update.
There are weeks that I play this 2-3 times a day, and then a couple of months of not at all. I usually win it. If I am overwhelmed, I joust and bet a land (and 90% I win - this gives me the opportunity to 'conquer' 3 counties per round, instead of just 1 with normal attack).
EDIT: I don't know if this counts as old, but I've restarted playing FTL - Faster Than Light. I sometimes also play StarControl II, but once every couple of years for a weekend or so.
There are weeks that I play this 2-3 times a day, and then a couple of months of not at all. I usually win it. If I am overwhelmed, I joust and bet a land (and 90% I win - this gives me the opportunity to 'conquer' 3 counties per round, instead of just 1 with normal attack).
EDIT: I don't know if this counts as old, but I've restarted playing FTL - Faster Than Light. I sometimes also play StarControl II, but once every couple of years for a weekend or so.