Henman attended the Longbridge School for boys between the ages of five and seven, and was enrolled in the private Dragon School in Oxford from seven to 11. He excelled in all sports but was always best at tennis. But Henman was small for his age, a factor which would bode against him in the future. In 1985, he was appointed the school's captain of tennis and led the school's tennis team to win 21 out of 27 matches. He remains to this day the only pupil who has won both the school's junior and senior tennis tournaments in the same year. From the age of eight until his introduction to the Slater Squad, Henman received coaching from the David Lloyd Tennis Centre, where he was given personal lessons by former professional player Onny Parun from New Zealand. In retrospect, Parun stated that Henman's greatest strength "had always been his head." David Lloyd noticed the same mental toughness and was impressed.