this post was submitted on 11 Dec 2023
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Gaming
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This varies between "functionally impossible" to "tricky but doable" depending on the game. Generally speaking getting old games to run via using the original media is very hard. The easiest way is to buy them again on GOG.com. Second easiest is to quasi-legaly (legal in my country, illegal in others) download a pirated copy of the GOG version. The other options I'd need to know which game before I promise anything.
I have to re-buy games I already own? ๐ซ
You're trying to get games built for a different OS (e.g., Win98) to run on your current OS. If it doesn't work out-of-the-box, you're going to need to seek a solution that either requires emulation or significant hoops to jump through. For example: if the game was built for a 16-bit machine, and you're running a 64-bit version of Windows, the game is just not going to work natively.
DOSBox may not work as it's an x86 emulator intended for MS-DOS. However, earlier versions of Windows (up to Win95) were just shells to MS-DOS. So, if the games in question were built for Win95 or earlier, DOSBox could be an option. I've also successfully installed Win98 on DOSBox but have run in to issues with drivers.
It may be best to simply list the games you're trying to get running and seeing if someone else has gotten them to run in Win10.