If you mean from the computer to your Xbox HDD, I think the answer is yes. You'll need a piece of software called Xport 360 installed on your computer so that you can copy the season files onto your hard drive. You'll also need to figure out exactly where your existing APF 2K8 saved files are located on the hard drive (it's a lot more crowded on a hard drive than on a USB memory stick, and it's not obvious where the game folders are being held -- you can do it by digging around a bit, though). Provided you have the above figured out, you should be able to copy the season files over and use them.
My feeling is that the USB stick approach is the path of least resistance, but this is worth trying as well just to see if it can be done.
Test it out and let us know. Good luck.