Old games compatibility is like a bell shaped curve. Late 90's onwards games are often easy to run with a little tweaking. Pre-Windows MS-DOS games are also fairly easy via DOSBox, ScummVM or some other emulator. Unfortunately there's this "bump" sometime around the mid 90's, where games were written as 16-bit Windows (not DOS) games during the Win 3.11 to Win 95 transition that have no official emulators and don't run well natively.
First thing to note is your OS:-
64-bit OS's support 64-bit and 32-bit but not 16-bit.
32-bit OS's support 32-bit and 16-bit but not 64-bit.
Your best bet is to maybe try installing 32-bit Windows XP on a VM or use Microsoft's official Windows 7 "XP Mode" (I don't mean "Run this program in compatibility mode for" tab in the typical right-click on .exe file settings, but rather the official "XP Mode" and related Virtual PC tools Microsoft released that creates a virtual 32-bit Windows XP installation running like a VM). I think
this and
this are the right links (you need both "XP Mode" and "Virtual PC"). Basic instructions
here. Best of luck.