Grossman's most successful season was in 2006 when he helped lead the Bears to a conference title and an appearance in Super Bowl XLI.

His senior season culminated when he led the Panthers to a 35–14 victory over the Homestead High School Spartans in the Indiana Class 5A state championship game.

[2] Bloomington High School South retired his jersey in the summer of 2007 to commemorate his success during the Chicago Bears' 2006 season.

[6] After redshirting his freshman year in 1999, Grossman competed for playing time with returning starter Jesse Palmer and the top high school recruit in the country Brock Berlin, in 2000.

Grossman had gotten the opportunity to start after completing 13 of 16 pass attempts for 232 yards and two touchdowns against Mississippi State the week before in the Gators' only SEC conference loss of the season.

[7] Grossman solidified his position as Florida's starting quarterback during the next two games by throwing for over 500 yards, eight touchdowns and no interceptions in lopsided wins over LSU and Auburn.

[13] As a junior team captain in 2002, Grossman led the Gators in the famed "Slingin' in the Rain" game against the Tennessee Volunteers, in which he threw three touchdowns and 22 completions in 32 attempts en route to a 30–13 victory over the Vols.

[14][15] Grossman led the Gators to the 2003 Outback Bowl, where they lost to the Michigan Wolverines 38–30 despite his completing 21 of 41 passes for 323 yards and two touchdowns.

[24][25] Head coach Dick Jauron kept Grossman sidelined as a rookie in favor of veteran quarterbacks Chris Chandler and Kordell Stewart.

[28] Criticism of his durability intensified when Grossman suffered a season-ending ACL injury during a Week 3 loss to the Minnesota Vikings.

[30] He completed 11 of 16 passes for 166 yards for a touchdown and interception in a 24–17 victory against the Green Bay Packers during the following week on Christmas Day.

[31] Grossman struggled to anchor the Bears' offense in his first career playoff start, completing 17 of 41 passes for 192 yards for one touchdown and an interception in a 29–21 loss against the Carolina Panthers.

[35][36] Grossman's work ethic drew criticism when he admitted that he was not adequately prepared to play and later claimed the game to be "meaningless.

[38] His inconsistent performance drew criticism, and calls for Smith to bench Grossman in favor of the veteran Brian Griese.

[41] He temporarily silenced his critics by leading the Bears to a 27–24 victory over the Seattle Seahawks, completing 21 of 38 passes for 282 yards and one interception, fumble, and touchdown.

[51] Though Grossman only played for roughly one half, he led the Bears to a 17–6 victory over the Oakland Raiders with a 59-yard touchdown pass to Bernard Berrian.

[55] Grossman was forced to relinquish his starting position to Kyle Orton, who had previously temporarily relieved him after his 2005 preseason injury.

[64] Grossman remained the team's back-up quarterback until week nine against the winless Detroit Lions when he was called to replace Orton who left the game due an ankle injury.

[66] Brian Urlacher defended Grossman after the game, commenting, "We've got a quarterback who comes in off the bench and leads us to a victory, and they boo him right out of the gate.

[67] Grossman received his final snaps of the season in the following week, when he was called to relieve Orton in a 37–3 loss to the Green Bay Packers.

[74] Grossman only played in a single game during the 2009 season, temporarily relieving Matt Schaub in a 23–18 loss to the Jacksonville Jaguars.

[78] The Redskins fell behind the Dallas Cowboys early in the game, but Grossman threw for 322 yards, four touchdowns, and two interceptions to erase a 20-point deficit.

[82] Grossman started the 2011 season with a win against the eventual Super Bowl champion New York Giants, completing 21 of 34 attempts while throwing for 305 yards and two touchdowns.

[83] Grossman would lead the Redskins to a 3–1 start before being benched in a four-interception week 6 performance against the Philadelphia Eagles in favor of Beck.

He helped the Redskins snap a six-game skid the next week with a 23–17 win over the Seattle Seahawks in which he threw 314 yards, two interceptions, and two touchdowns.

[89] On December 22, the Browns offered Grossman a one-week $53,529 NFL veteran league minimum contract after losing Johnny Manziel and Brian Hoyer to injuries.

[93] Grossman's gunslinger attitude was illustrated in his desire to throw long passes, similar to his youth idol, Brett Favre.

[97] However, during a Divisional Round game in the 2006 playoffs, he threw a 68-yard touchdown pass to Berrian on the opening play of the Bears’ second drive.

The cover featured Grossman with teammates Devin Hester and Tommie Harris posing with bears in a museum exhibit.

[110] It was reported that Grossman absorbed a $680,000 loss on his September 2008 purchase of a 36th floor condo in the Trump International Hotel & Tower Chicago when it sold in January 2010, losing 25% of his initial investment.