I've had Windows 95 mess up twice like that at the time 
- I had a RAMdisk for a while, first set to 20MB (out of 32MB RAM), then lowered it to 3MB to free up some more RAM for Windows/programs/etc. ... then one day I decided to set it to 20MB again (forgot why) and the computer suddenly froze I rebooted only to see it fail to find win.com, then realized the whole Windows folder was corrupted ... I reinstalled Windows on the second partition, copied Windows's files over, ran chkdsk to get most of the files back (desktop, etc.), and all was fine ... or almost, I lost the old wallpaper I drew in Paint the day I got that computer 
- About a year later, I forgot how that one happened but Windows glitched up again after a crash, it still ran but a lot of things were broken (corrupted registry?), like I couldn't run Internet Explorer (and some other programs) or even drag&drop ... eventually I installed Windows on the second partition again and it ran fine, except I never got Internet access on it (I had dialup), so I ended up with a dual Windows 95 boot ... broken with Internet access, and non broken without (this stayed for almost a year until I got Windows 98)
At least I've never had problems like this again, I'm even nearing 3 months of uptime now 
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