Tony Bennett's tenure as head coach of Virginia from 2009 to 2024 was marked by significant achievement. Leading Virginia to the NCAA Division I tournament championship in 2019, Bennett's leadership saw the team secure six ACC regular season titles in 2014, 2015, 2018, 2019, 2021, and 2023. Furthermore, his strategic approach to coaching also led the team to two ACC tournament championships in 2014 and 2018. This effective coaching style was recognized by multiple awards, including three Henry Iba Awards in 2007, 2015, and 2018, and being twice named Naismith College Coach of the Year in 2007 and 2018.

His dedication to the sport and his team resulted in Bennett being twice honored as AP National Coach of the Year in 2007 and 2018 and NABC Coach of the Year in 2018. His effective coaching style was also recognized with the Jim Phelan Award in 2007. Additionally, under Bennett's guidance, Virginia consistently improved, culminating in multiple 30-win seasons, and in 2014, Virginia won the ACC regular season and ACC Tournament titles. His coaching strategies, built on "five pillars" that focus on humility and grace, have been integral to these successes.

Upon his retirement in 2024, Bennett left a powerful legacy. He had developed several NCAA All-Americans and NBA draft picks, with players such as Malcolm Brogdon, Joe Harris, and Klay Thompson excelling in NBA shooting. Bennett's Virginia teams were also known for their strong defense, and he led Virginia to a 60–26 record in rivalry games against Virginia Tech, Louisville, Maryland, and North Carolina. His influence extended beyond the court, with Bennett and his family pledging $500,000 to fund a career development program for members of the Virginia basketball program.

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