His Wilson football teams won two Lancaster-Lebanon League Section 1 titles, the first his freshman year (2000[3]) and the second his junior season (2002).

His 2002 Wilson Bulldogs squad finished their regular season undefeated with a record of 10–0 and were the 2002 PIAA District 3 AAAA runner-up, falling to Central Dauphin in a thrilling championship game.

He rotated at QB with junior Ian Firestone in the Week 1 storm-delayed win vs Harrisburg but would start the final 10 games for the Bulldogs and play the majority of the positional snaps.

[3] Henne led come-from-behind victories against Wilson's first three opponents – Harrisburg, Stroudsburg, and Boyertown – before a setback at Cedar Crest to open League play.

Henne's Wilson team would win their next six contests, including a thrilling comeback victory at Reading, before falling in the 2000 District 3 AAAA semifinals to eventual champion Cumberland Valley, 21–7.

[3] His freshman season was an overwhelming success, with the team finishing 9–2 and earning a share of the Lancaster-Lebanon League Section 1 title (with Cedar Crest and Reading).

[2] At the end of his junior year in 2002, having been offered forty scholarships from various collegiate athletic programs, Henne narrowed his college options down to five schools: Miami, Michigan, Georgia, Tennessee, and Penn State.

The Monday prior to the season opener against the Miami RedHawks, Michigan head coach Lloyd Carr announced Gutierrez would start even though he was suffering from a sore shoulder.

[17] Alongside freshman running back Mike Hart, he galvanized an explosive offensive unit that featured receivers Braylon Edwards, Jason Avant, and Steve Breaston.

Henne's freshman season was highlighted by a triple-overtime win over in-state rival Michigan State[18][19] and a record-tying performance in the Rose Bowl against Texas.

[23] The sophomore quarterback was particularly scrutinized after his performance in a close loss to Notre Dame, in which he completed fewer than half of his pass attempts and lost a fumble on the goal line.

[26] For the third straight year Michigan concluded their season by losing to Ohio State and then dropping their bowl game, this time to Southern California.

[28] The first game of the season ended in disaster for Michigan, a loss to Appalachian State that was considered one of the biggest sports upsets of all time.

[30][31] In the final regular season game, Michigan fell to Ohio State 14–3, completing an 0–4 career record for Henne and fellow seniors Mike Hart and Jake Long against the Buckeyes.

Henne was named the MVP of the game after he led his team to a 41–35 victory over the Gators and reigning Heisman Trophy winner, Tim Tebow.

Though he led the Dolphins offense to ten points in the final 20 minutes of the game, he also had an interception returned 31 yards for a touchdown by Eric Weddle.

[49] In Week 17 against the Pittsburgh Steelers, Henne had gained 140 yards on 16–of–20 passing with one touchdown and interception, but had to leave the game with an eye injury.

[60] His job as starter was thought to be in question during the off-season when it was rumored that the Dolphins sought to acquire Kyle Orton from the Denver Broncos.

Coupled with the acquisition of Carolina Panthers quarterback Matt Moore and rookie draft pick Pat Devlin, it was unclear if Miami would continue its commitment with Henne.

The Orton rumor eventually fizzled and Devlin was waived and signed to the practice squad, leaving Moore and Henne as the two quarterbacks on the active roster.

[61] On Sunday October 2, 2011, in a game against the San Diego Chargers, Henne hurt his left shoulder at the end of a run on a broken play on the Dolphins' second possession and did not return.

[65] Henne and Steve Young are the only two players in NFL history since the merger to not start the beginning of a game and throw 4 touchdowns without an interception.

[68] Following a disappointing first half in the 2014 home opener in Week 3, Henne was benched in favor of rookie first-round draft pick Blake Bortles.

[77] Henne did not play a snap all season but won his first championship when the Chiefs defeated the San Francisco 49ers 31–20 in Super Bowl LIV.

[86] On January 21, 2023, Henne replaced an injured Patrick Mahomes and led a team playoff record 98-yard touchdown drive in the AFC Divisional Round victory over the Jacksonville Jaguars.

[87][88] On February 12, 2023, after the Chiefs defeated the Eagles in Super Bowl LVII, Henne announced via his Instagram that he would be retiring from the NFL.