Here is a quick tutorial on how to emulate Windows 3.11 on iOS. This should also work with any other DOS-based version of windows. To get emulation up and running, you will need jailbroken device.
First, you’ll need to install DOSPAD, MS-DOS emulator based on DOSBox. You won’t find it in main Cydia repository, so you’ll need to add custom repository. Open Cydia, then go to Sources. Select Edit and then Add, and enter http://cydia.myrepospace.com/Jujul98. Once repository source has been added, tap on it, select All Packages and then select DOSPAD to install it.
Once DOSPAD is installed, you’ll have a working MS-DOS environment in which to install Windows 3.11. DOSPAD mounts Documents folder as C:\ drive, so to get new files to access from emulator just copy them via SSH/FTP to Documents folder.
Now you’ll need installation files for Windows 3.11. Create install directory and copy all installation files in there. If you don’t have original Windows 3.11 floppies, Google is your friend. Copy install folder to Document folder on iPhone/iPad. Open DOSPAD an run setup from install directory. Go through Windows installation process (shouldn’t take long) and once it’s finished you’ll have working Windows 3.11 installation.