No, iTunes can not do this. No software is capable of burning cross fades to mp3 files if you are burning the mp3s to a data disc.
To get cross fading you must burn the disc as an Audio disc.Tthe best app, I think, on the market for Mac OS X is
Roxio Jam. This app will allow you to create Audio discs with all the cross fades you can handle.
This thread has been closed by the system or the community team.
You may vote for any posts you find helpful, or search the Community for additional answers.
Burning MP3 Files and Crossfading them.
Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple Account.