Hard to say which games are truly dos designs sometimes.
Once something runs on Windows, is it still a dos game?
I think the oldest games I will 'try' to play, are Steel Panthers, V4Victory, Construction Set 2 Tanks, Steel Panthers 3 (if the download cooperates), original Civilization and original Heroes of Might and Magic (often just for the nostagia hit). I have a few titles on the site mentioned in another thread that might interest me if they cooperate.
I think I am likely among many when I say, often older titles from a long way back, run better than a lot of supposedly 'better' programs of today.
I've seen the comments, the AI was better, the simulation superior, all while having seemingly dreadful graphics when compared to today's fare.
In a lot of cases, older software is amazingly similar to older board games. Not as complex, complicated and glitzy, and yet, better at providing the fun.