Terry Glenn was drafted in the first round (seventh overall) of the 1996 NFL Draft by the New England Patriots. He signed a six-year, $12 million contract. Glenn recorded 90 receptions for 1,132 yards and six touchdowns in his rookie season. At the time, his 90 receptions were the most ever in a single season by a rookie in NFL history. Wide receiver Anquan Boldin went on to catch 101 passes his rookie year during the 2003 NFL season for the Arizona Cardinals. Patriots head coach, Bill Parcells, once referred to Glenn as “she”, but after the 1996 season said he was wrong and Glenn was a winner. However, Parcells left New England after Glenn’s rookie season and Glenn went into a four-year stretch of personal difficulties and inconsistent play. In 1999 and 2000, he was the Patriots leading receiver. He signed a six-year, $50 million contract extension during the 2000 season. In the lead-up to the 2001 season, Glenn ran into a host of off-field issues. First he was arrested for domestic assault, and later he was suspended for the first four games of the season due to failing a drug test. Shortly before the season, he left training camp early due to a pay dispute. Glenn did end up playing for the team after serving his suspension, but following injuries and more disputes with the coaching staff, head coach Bill Belichick deactivated him for the rest of the season. Terry Glenn only wound up playing in four games in 2001, most notably catching the first career touchdown pass thrown by Tom Brady in a game against the San Diego Chargers on October 14th. The Patriots went on to win Super Bowl XXXVI without Glenn, and he did not receive a Super Bowl ring.

Before the 2003 season the Packers traded him to the Dallas Cowboys. Against the Kansas City Chiefs in 2005, Terry Glenn caught a touchdown pass on a flea-flicker and rushed for a touchdown on an end-around, both trick plays. Glenn finished the 2005 season with 63 receptions for 1,136 yards and 7 touchdowns, the most receiving yards he had amassed in a single season since 1999. Before the 2006 season, he signed a five-year, $20 million contract extension with Dallas. In 2006, he recorded another 1,000 yard season and six touchdowns. Glenn missed the first fifteen games of the 2007 season and had been unable to even practice due to pre-season arthroscopic knee surgery. He returned to practice on December 12, 2007 but did not play in Week 15 against the Philadelphia Eagles and did not fly to Carolina for the Week 16 game. He made his season debut in Week 17 against the Washington Redskins. Terry Glenn was released by the Cowboys on July 25, 2008, due to health concerns over his right knee, and not signing an injury clause. Terry Glenn died at the age of 43 following a one-vehicle rollover traffic accident on November 20, 2017, in Irving, Texas, near Dallas, which left his fiancee slightly injured.