Q: I purchased a game (Texas Hold’em) for my old fifth-generation iPod, which has since been stolen and replaced with a new iPod classic. However, this game will not sync with my new iPod classic, and in iTunes it says it is only compatible with the fifth-generation iPod. Any ideas how to make it sync to the new iPod classic?
A: Unfortunately, games that were purchased for the fifth-genereation iPod are simply not compatible with the iPod classic or iPod nano (video). This incompatibility is due to the fact that these new iPod models use a different hardware architecture, and the games had to be recompiled for the new hardware. Sadly, however, Apple chose to not offer an upgrade path for previous fifth-generation iPod users, requiring the games to simply be re-purchased again for the new iPod models at the full retail price.
Therefore, you will have to re-purchase the game from the iTunes Store for your iPod classic. Alternatively, you can try contacting the iTunes Store customer service department to see if they can be of assistance in allowing you to download the game again to include the iPod classic version, but they will likely also tell you that you need to purchase the game again for your iPod classic.