Old but still difficult to beat: Chessmaster 2100, Fritz 3, Chess Genius etc
It's quite interesting to go back to the early development of chess programs. I remember, back in 1992 when I bought my first 286 PC and then got my Chessmaster 2100. I played the program regularly, and beat its strongest championship setting, it did print certificate for my winning too. Nowdays it's a dream to even draw with the latest Chessmaster if your are not a master. Just for curiousity I searched if the old programs are still out there and the result is...YES somebody got the link for it, check it out below:
LINK FOR OLD CHESS PLAYING SOFTWARES
Amazingly the program runs on my Windows Vista using DosBox, still like it much although the graphic is not that fantastic!! No installation is needed, just create a folder, copy the files and run it from there. DosBox link is here: [DosBox Link]
Note that if you are not familiar with the old DOS commands, it would take a while for you to figure out how the DosBox works for you.