Boselli played with the Jaguars until 2002, proving to be one of the franchise's most successful and popular players. He was then drafted by the Houston Texans as the first overall pick in the 2002 expansion draft, but was unable to play with them due to injuries.
Boselli was selected as the second pick of the 1995 NFL Draft, the first-ever draft pick of the new Jacksonville Jaguars franchise. As a result of his professional success and local popularity, Jacksonville-area McDonald's restaurants offered the "Boselli Burger" in his honor for a period of time.
He was selected by the Houston Texans in the 2002 expansion draft, but injuries prevented him from playing and he retired after the season. As a sign of his success in Jacksonville, on October 8, 2006, he was the first player inducted into the Pride of the Jaguars (the team's Hall of Fame) and signed a symbolic one-day contract allowing him to retire officially as a Jaguar. Boselli has been listed on the Pro Football Hall of Fame Preliminary Nominees list every year since 2009. NFL Films has named Boselli the 6th greatest player not inducted into the Pro Football Hall of Fame.
Boselli participated in numerous business ventures during and after his professional football career. He, plus former teammates Mark Brunell and Bryan Schwartz, invested in seven Mattress Firm bedding stores in Jacksonville. By the time Boselli left for Texas in 2002, he had sold his interest in the company. Boselli and Brunell own all Whataburger franchise locations in the Jacksonville area. He also works as the offensive Line coach at the Episcopal School of Jacksonville, on the same coaching staff as Brunell.
Since 2005, Boselli has lived in Ponte Vedra with his wife, Angi and their five children: Andrew, Adam, Ashli, Alexis, and Ansli. Boselli has lost a significant amount of weight and now participates in triathlons.
In 2007, Boselli was hired as a color commentator on regional NFL telecasts for Fox, teaming with Ron Pitts. In his rookie season as a televised commentator, Boselli drew praise as one of the best in the business.
From 2009-2012, he worked as a game analyst and sideline reporter for Westwood One's coverage of the NFL.
Beginning in 2013, he joined the Jacksonville Jaguars radio play by play team.
Boselli was a former co-host on 1010 XL with Dan Hicken and Jeff Prosser each morning from 6-10 am on Sports Final Radio.
Tony and his wife, Angi (the former Miss California Teen USA 1987), created the Boselli Foundation during 1995 in Jacksonville to work with at-risk youth and help them to cultivate high self-esteem and to succeed at home, at school and at play. Beginning in 2007, Tony has spent substantial time working on projects with the foundation. He overcame opposition from local politicians when the Boselli Foundation proposed renovating and reopening a closed community center and has significant support.