If there is a direct quote, then the book contains a typo. The correct phrase is “come out ahead” -because “ahead” is one word. But as written it sounds like a team exits the situation transformed to a literal head.

This word is formed from the prefix ” a ” meaning “in or at” and “head”. Where do you get a head and “head”?

As you correctly surmised, the phrase, during play, asks which team will win. (The best teams to play) When you come out ahead, you come away from some event in a better situation than you started, or than some other person. You may be coming out ahead of someone you know or a close friend, or you may, or may not be, having outspoken opinions about yourself or your past self?

How did he create the article? This is an extremely common phrase, though in this case it would appear that the author mistyped it.