His tennis career was launched in 1982 and Gilbert in the same year he won his first singles title in Taipei. The first doubles title won Gilbert in 1985 in Tel Aviv. During his career he won 20 singles titles and three doubles. In January 1990, he reached number 4 in the world rankings. In the 1988 Olympics he won the bronze medal.
Gilbert finished his career in 1995, since then he has been working as one of the most successful tennis coach in the world. He was responsible, among other things eight years Andre Agassi. During this time, Agassi won six Grand Slam tournaments. The collaboration ended in 2002. Thereafter, Gilbert worked with Andy Roddick, he also led the U.S. Open title in 2003. The partnership ended in 2004.
His book " Winning Ugly - Mental Warfare in Tennis " is considered one of the best books on the subject of " tennis " strategy. He works as a commentator for ESPN.
2006 and by the end of 2007, he coached the British rising star Andy Murray.