Installation of Windows 98SE using VMware Player


There are different reasons for using a Virtual Machine. One of the reasons is just to run Legacy Software. If you have the setup files for all your software you can create a new Windows 98SE VM and copy then over to the VM and install your legacy software. Software may also be on a CD/DVD drive and may require the CD to be present in an optical drive to launch the setup. The software may also have a protection USB that needs to be connected to the VM in order for the software to launch. Your hardware may also use Serial Ports. Your specialised hardware may need access to a Bootable Floppy Disc. I will first list some useful USB adaptors if you are trying to connect to legacy hardware.


If your software is on a CD/DVD you may however have an issue because the host PC you wish to virtualise your VM on does not have a CD/DVD drive. Firstly if you have an old computer with a CD/DVD drive then you should use WinImage to convert your CD/DVD to an ISO which can subsequently be loaded as a Virtual Drive in the VM. For more details see WinImage and Connecting to Legacy Hardware. If you do not have a CD/DVD drive then you’ll need a CD/DVD to USB one. I recommend the following (please use the affiliate links to help fund my guides).

Floppy Discs

You may have even older software… and require a floppy drive. Firstly if you have an old computer with the Floppy drive then you should use WinImage to convert your Floppy Discs to a FLP file which can subsequently be loaded as a Virtual Drive in the VM. For more details see WinImage and Connecting to Legacy Hardware. If you do not have a Floppy drive then you’ll need a USB one. The most highly rated virtual USB to floppy drive is the Esynic one. Note if you are needing a floppy drive to use as a boot drive. I recommend the following (please use the affiliate links to help fund my guides).

USB Ports

The next is if you are wanting to interface to some legacy hardware. If the hardware has a USB port, then most modern computers have USB ports and with VMware player you can readily connect to legacy devices over USB.

If your computer is brand new and only has USB Type-C connectors then you may need a USB Type C to USB adaptor. I used these on my XPS 13 9365 (please use the affiliate links to help fund my guides).

Serial Ports

For Serial Ports I’ve found the following by plugable to be the most useful and have tested them on several legacy scientific instruments in the lab. The following are affiliate links to and No driver is required for the Windows 10 Host by the Windows XP guest will require the driver listed here.

Download Windows 98SE ISO

The website WinWorld appears to have ISOs and Serial Key:

Use the OEM ISO and the Serial Key that they list. Install 7zip and use it to extract the ISO:

You should now have the ISO file:

Setup VMware Player

You need to have VMware Player installed on your Windows 10 Pro 64 Bit host:

Open up VMware Player:

Select Player → File → New Virtual Machine:

Select I will install this Operating System later and select Next:

Select Microsoft Windows and then select Next:

Input your VM’s name and select it’s Location. I’m going to use my secondary SSD D:\Win98SEVM. When happy select Next:

Use the default settings here and select Next:

Select customise hardware:

Under New CD/DVD select Use ISO Image file and select Browse:

Select the Windows 98 Second Edition ISO and select Open:

Under Network Adapter uncheck Connected and Connect at Power On. This will ensure that the unsafe version of Windows does not get connected to the internet. Select OK:

Select Finish:

Installing Windows 98SE

Select the Play Button to Start the VM:

VMware will also tell you the magic keyboard shortcut keys. [Ctrl] + [g] to take your mouse to the VM:

And [Ctrl] + [Alt] to take your mouse away from the VM.

Press [↓] and select Boot from CD-ROM and press [Enter]:

Select Remind me later if you get a prompt for VMware Tools:

Select Start Windows 98 Setup from CD-ROM:

Press [Enter]:

Select “Configure Unallocated Space” and press [Enter]:

Press the [↓] key and select “Yes Enable “Large” Disk Support” and press [Enter]. This is still tiny by todays standards:

Ignore any mention of the floppy drive A: and press [Enter]:

Your VM will restart, you will see the Legacy BIOS splash screen:

Once again press the [↓] key and highlight Boot from CD-ROM. Then press [Enter]:

Select the first option and press [Enter]:

Windows 98SE will then format the virtual hard disk:

Press [Enter]:

Select [Continue]:

Use the default directory and press [Enter]:

Select Typical and press [Next]:

Select the Recommended Option and press Next:

Type in your Computer’s name and press Next:

Select your Country and select Next:

Select Next:

Your Windows 98SE VM will restart:

You will see the Virtual Legacy BIOS Splash screen and Windows 98SE logo:

Input the generic Product Key and select Next. There was no product activation with Windows 98SE as many users never had an internet connection:

Select Finish:

The setup will configure on the Virtual Hardware:

The VM will restart, you will see the Windows 98 splash screen followed by the Virtual Legacy BIOS splash screen followed by the Windows 98 splash screen:

Windows 98SE will setup hardware:

Select your time zone and select Apply:

Then select OK:

The System Settings will Update and the Windows 98 VM will once again restart:

You” once again see the Windows 98 splash screen, the Virtual Legacy BIOS splash screen and the Windows 98 splash screen again:

Select OK to log in:

Windows 98SE will Add New Found Hardware:

It will Update the System Settings again:

You will see the Welcome to Windows 98 splash screen. Uncheck “Show this screen every time Windows 98 starts” and select Close:

Installation of VMware Tools

Select Player → Manage → Install VMware Tools:

You will be prompted to Download and Install VMware tools (note the download will come via your host PC and not via your guest PC).

The tools will download:

You will get a message about the CD-ROM Drive. Select Yes

The VMware Tools will extract:

Select Next:

Select Next:

Select Install:

Select Yes:

Select Finish:

Select OK:

Select Finish:

Select Yes to restart:

You will see the Windows 98 splash screen, the Virtual Legacy BIOS splash screen and the Windows 98 splash screen again:

Select OK to log in:

You can now resize the VM however the first time you do this, it won’t resize.

Right click the Desktop and select Properties:

Now select Settings and change the slider to the maximum position:

Select Apply and then OK:

Now the screen will be too big, but select Yes anyway:

When you resize the Window, the VM will now resize with it. Select cancel at display properties:

That’s you got VMware tools installed:

Installing System Drivers

Unfortunately VMware Tools doesn’t include all the system drivers required for the VM. You should install the following in order.

Unofficial Service Pack:

Intel Chipset

Intel USB 2.0:


Creative Sound Driver:

Direct X 9.0c:

Logitech Mouse

Drag and drop the files to the Desktop of the Windows 98SE VM:

Now you can install them one by one, starting with the Service Pack. Select Yes:

Close down the Overview:

Select OK:

Select Yes to Restart:

Now install the Chipset Driver:

Select Next:

Select Yes:

Select Next:

Select Yes to Restart the VM:

Once you’ve logged in Windows 98SE will try to install a driver:

Select Next:

Select the Recommended Option and then select Next:

Select specify a Location leaving the default C:\WINDOWS\CATROOT and then select Next:

Select Next, Next and Finish:

You will have to install multiple other devices and restart the VM a couple of times to fully install the Chipset drivers. You can now install the remaining drivers which follow a very similar procedure.

Addition of Legacy Devices

You can add more hardware such as a floppy drive (virtual floppy drive with .flp images or an onboard/USB floppy drive), serial port (onboard or USB serial port) and parallel port (onboard or USB serial port). Power off the VM and right click your VM and select settings:


Select Add Hardware:


Select yes at the User Account Control:


You may add a floppy drive, parallel port and/or serial port depending on the legacy hardware you wish to connect to:


I advise not setting the Floppy to Connect at Power on otherwise the system will try to boot from the Floppy Disk before the HDD> This can be amended in the BIOS setup however:











These and USB devices can be accessed via the Player Menu. Each optical drive, floppy drive, network adapter, serial port, parallel port and soundcard will be listed separately. Below these any USB device are listed. If the USB devices have a tick they are connected to the VM (and removed from the Host OS). The Ability to connect to all of these Removable Devices and the installation of legacy Windows OS make the VM very powerful:



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