King_DuckZ

@A_Random_Idiot well for example Alpha Centauri and even Civ 2 were really easy for me. I used wine without any wrappers, I simply set an older Windows compatibility version in winecfg. StarCraft also worked easily though I wasn’t able to set it to full screen properly on Wayland and had to re-login into Xorg for it. Let’s see if OP provides us with more details

@noumenon it depends on how old! Are you talking Windows 95 old or Dos old? Either way, step 1 I suggest is to start from Linux. Step 2 depends on your answer to the above :)