There is no direct way to copy files from an iPod to a Zune, but here with 2 softwares below, you can use them to transfer iPod video/songs to Zune.
How to Transfer iPod to Zune
part 1: Transfer iPod songs/video to PC easily with AVCWare iPod to iPod/Computer/iTunes Transfer
iPod to Computer Transfer automatically transfers your iPod and iPhone music, video, playlist, photos back to PC and iTunes. Backup all your music and video in a couple of clicks. If you own more than one iPods, AVCWare iPod to iPod/Computer/iTunes Transfer can simultaneously manage all the iPods in the same interface, you may transfer files among these iPods by drag-and-drop.
And this iPod to PC Transfer fully supports the latest iPhone OS 3.0, iPhone 3GS, iPod touch FW 3.0, and iTunes 8.2. Free trial is surported.
$24.95
Part 2: Convert iPod to Zune with Tipard iPod to Zune Converter
After you have transferred iPod Video to PC, just download and install this iPod to Zune Converter, which can easily and quickly convert videos to Zune/Zune 2.
Tipard iPod to Zune Converter is a professional iPod to Zune Converter, which can not only convert iPod Videos/songs to Zune/Zune 2 for entertainment, but also support all video formats including MPG, MPEG, MPEG2, SWF, FLV, VOB, MOD, MP4, H.264, M4V, AVI, WMV, 3GP, 3GPP, MOV, DivX, XviD, QuickTime Video, etc, even the High Definition video files(HD/AVCHD videos), such as TS, MTS, M2TS, HD MPEG 2, HD MEG4, HD WMV, HD MOV, HD H.264, HD RM etc. And the converted files can be enjoyed on your Zune, Zune2, iPod, iPhone, Apple TV, PSP, PS3, Wii, Xbox, Sony Walkman, Sony XPERIA, Google Phone, BlackBerry and all the Mobile Phones.
Though this way of transferring iPod to Zune is a little expensive, but it can save your time and prevent you from hassling with all the re-ripping of tracks. If you want to transfer videos/songs from iPod to Zune, Just have a try this solution!