I am not sure it wouldn't, when it was released 95/98 were the highest operating systems. I would think the newer systems have all the programming the older versions had - but more. I could be wrong. According to EHow, you can play them on Win7 and XP http://www.ehow.com/how_6076089_can-games-run-windows-98_.html
Not a guarantee! Look it up, because I am no expert. Doesn't look hard though and if you have a good experience it isn't hard to find these games at great prices!