Yes, you can if you have Windows98SE. If you don’t have SE you cannot use the iPod as standard 98 does not have USB or Firewire support. You will have to follow these steps to configure your iPod under Win98SE.
I'm a passionate, long-time lover of Apple products, and was a civil draftsman and graphic designer before creating the iLounge web site. My prior projects include work for The Los Angeles Times' LATimes.com, and the company Creative Domain, where I developed websites for clients including Columbia Pictures, Disney, Fox Studios, Universal Pictures and Warner Brothers. As the Publisher of iLounge, I direct the site's community forums, photo galleries, iPod User Group, and general business affairs, which have grown under my watch to over sixteen million page views every month. I'm happily married with one daughter, one dog (Rocket the Wonderdog), one cat (Ferris), many iPods, iPhones, iPads, and two turntables.