I play The Web regularly on win7, should be possible on win8, or even on win10(maybe a virtual machine or a DosBox is needed on Win10, the free and great working Oracle VM VirtualBox is an option) but maybe it runs without a virtual machine.
Using a Dos emulator: The Web, Timeshock and BigRaceUSA are supported
http://www.dosbox.com/comp_list.php?letter=P