After serving with the United States Army and attaining the rank of First Lieutenant in 1956, he turned to teaching tennis after dropping out of the University of Miami Law School.

[5] Though he had only dabbled in the sport in high school, Bollettieri was the tennis director at Dorado Beach Hotel in Puerto Rico in the late 1960s when it was a Rockefeller resort.

[6] Moving to Longboat Key, Florida, in 1978, Bollettieri served as an instructor for the Colony Beach and Tennis Resort.

[8] Additionally, he was featured in the Nick Bollettieri DVD Collection, a set of ten instructional DVDs that cover a wide range of practice methods.

[9] Bolletieri personally trained the majority of the controversially loud grunters in tennis, leading to repeated accusations that he has been deliberately teaching grunting as a novel tactic in order to give his later generations of students an edge in competitive play.

I think that if you look at other sports, weightlifting or doing squats or a golfer when he executes the shot or a hockey player, the exhaling is a release of energy in a constructive way".

One year later, a division of Bollettieri's academy released a document calling grunting "unsportsmanlike" and acknowledging that it obscures the sound of string impact (as noted by Navratilova), resulting in "an increase in an opponent's decision error, and a slower response time".

[25][26] On May 18, 2008, Bollettieri was honored at the New York College of Health Professions with an honorary doctorate in Humane Letters for his contribution to the world of sports, fitness, and wellness.