My son is in the same boat. Late Sept bday. My wife and I moved him up a year entering grade school as we see that he can handle it academically and emotionally (and he is doing well as a freshman right now). We didn't even think about sports at that time, nor were we aware that people are doing the opposite (repeating a grade). So he has classmates that are 2 years older than he is right now. He is playing travel with his age group (not with his grade). I do find myself letting people know he is young for his grade when it comes to sports. This thread is a reminder for me to quit doing that.