It sounds like he cares about you and wants you to get some sleep so that you can do well at the cross-country meet.
If it's 12:30 am and your chatting a guy (who you might happen to like) and he says "You have a cross country meet tomorrow, you better get some sleep" what does this mean? Is this his way of saying he's done talking to you or does he actually care?
He knows about your dedication and he's trying to show you that he cares and is aware of your hobbies.
Both. He may be trying to show he cares but also may br tired as hell and wants to get some sleep. More than likely its both!