Have you ever faced the problem where a legacy DOS or Windows 95 & 98 runs perfectly on Windows XP/Vista/7/8, with or without compatibility mode, but refuses to print?
This is because legacy DOS or Windows 95 & 98 programs expect your printer to be connected to a LPT1 port, which is usually not the case anymore nowadays. If you want to enable printing to an USB or Network Printer for these legacy DOS or Windows 95 & 98 programs, follow these steps:

1) First, make sure you can print from within Windows to the desired printer, by printing a test page.

2) Next, go to Control Panel –> Printers
All of your printers should be listed, including the printer you want to set up for DOS printing.

3) Right-Click on the name of the printer that you want to set up for DOS printing and choose “Properties” from the pop-up context menu.

4) Click on the “Ports” Tab at the top of the Printer Properties Window.

5) Make a note of the exact name of your current printer port.

6) Select the “Enable Printer Pooling” checkbox. i.e. be sure that the box is checked.

7) Scroll up and/or down through all of your listed ports and click the “LPT1” port to place a checkmark in it.
Note: You should now have both LPT1 and your default printer port (from step 5) selected

8) Click “Apply” and “Ok”.

There you go! You should now be able to print from your  legacy DOS/Windows 95 & 98 programs to your USB/Network printer
The above steps essentially trick Windows to act as if the USB/Ethernet printer is connected to LPT1.
No need to use expensive third party tools such as Printfil or DOS2USB… this will do the trick as well!