Bollettieri did not play tennis until his junior year in college. He told The Times that:

"Before that I thought tennis was for sissies. By senior year, I’d made the team. Then I joined the paratroopers and was out of action for two and a half years. After that, I went to law school and started coaching tennis on Miami beach to pay for my books. This was 1955 so I was getting $3 for half an hour."