Tennis Confidential includes interviews with such all-time greats as Pete Sampras, John McEnroe, Arthur Ashe, and Jimmy Connors along with essays about the careers of other stars like Andre Agassi, the Williams sisters, Jennifer Capriati, and Anna Kournikova. Fein also reviews the careers of pioneering players like Martina Navratilova, Bjorn Borg, and Rod Laver.

Tennis Confidential tackles the issues that confront the sport today, from the media's fascination with teenage players on the women's tour to the changes in the game caused by new racket designs and tactical innovations. Fein also reviews the ten greatest matches in tennis history. He gives fans at every level a unique perspective on the game and its history.