Calendar syncing issue between iPod and Macbook Pro

I apologize if this post is in the wrong place. I don't post here much, but read often.

Anyways, my father is having an issue syncing his iPod Calendar to his Macbook Pro Calendar.

He has three devices:

1. Older iPod Touch which cannot use iCloud
2. Newer Macbook Pro with the Calendar using iCloud
3. 2nd gen iPad with the Calendar using iCloud

The Macbook Pro's calendar seems to sync fine with the iPad's calendar using iCloud. However, when he updates the calendar on the iPod Touch, and then plugs it in to sync with the Macbook Pro, the updated calendar events will not update to the Macbook Pro.

In iTunes, under Info, he has "Sync Calendars" checked as well as "All Calendars" under that. It will not sync.

Since all of my actual devices use iCloud, I am not too familiar with mixing iCloud and non-iCloud devices. Any suggestions I could try when I head over there over the weekend would be appreciated.

 

I thought about that, but I doubt my dad would want to set up yet another thing. I think he has enough to remember at this point. Is this setup just not possible? Should he abandon iCloud for all devices if one cannot use it?