Career Timeline of Colton Underwood: Major Achievements and Milestones

By Popular Timelines Editorial Team · Updated: February 27, 2026

From career breakthroughs to professional milestones, explore how Colton Underwood made an impact.

Colton Underwood is an American reality television personality and former professional football player. He played in the NFL as a defensive end after playing at Illinois State. He gained wider recognition as a contestant on the 14th season of The Bachelorette before becoming the lead of the 23rd season of The Bachelor. Notably, he is the first lead in The Bachelor franchise to publicly come out as gay.

Sections (3)

Full Timeline Early Life & Education Career & Achievements

May 10, 2014: Signed by San Diego Chargers

On May 10, 2014, Colton Underwood was signed as an undrafted free agent by the San Diego Chargers.

September 23, 2014: Returned to Chargers

On September 23, 2014, Colton Brown-Underwood returned to the Chargers and was signed to their practice squad.

2014: Signed by San Diego Chargers

In 2014, Colton Underwood was signed as an undrafted free agent by the San Diego Chargers.

September 5, 2015: Waived by San Diego

On September 5, 2015, Colton Underwood was waived by San Diego.

December 1, 2015: Signed to the Oakland Raiders' practice squad

On December 1, 2015, Colton Underwood was signed to the Oakland Raiders' practice squad.

January 2016: Founded Colton Underwood Legacy Foundation

In January 2016, Colton Underwood founded the Colton Underwood Legacy Foundation to raise money for cystic fibrosis research and medical equipment.

August 29, 2016: Released by the Raiders

On August 29, 2016, Colton Underwood was released by the Raiders.

January 2018: Legacy Project began

In January 2018, the foundation began the Legacy Project, with the goal of delivering AffloVests to children in 50 US states.

September 4, 2018: Announced as the star of 'The Bachelor'

On September 4, 2018, ABC announced that Colton Underwood would star in the 23rd season of 'The Bachelor'.

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September 21, 2018: Filming for 'The Bachelor' began

On September 21, 2018, ABC announced that Colton Underwood had started filming 'The Bachelor' and met three contestants on 'The Ellen DeGeneres Show'.

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April 14, 2021: Production for Netflix unscripted series

On April 14, 2021, Variety reported that Colton Underwood was in production for his own unscripted series at Netflix.

December 3, 2021: 'Coming Out Colton' premiere

On December 3, 2021, the six-episode series 'Coming Out Colton', produced by Jeff Jenkins, premiered on Netflix. The series received major criticism.

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2024: Competed in 'The Masked Singer'

In 2024, Colton Brown-Underwood competed in season eleven of 'The Masked Singer' as "Lovebird" and was eliminated on "Transformers Night".

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August 18, 2025: Co-hosted dating reality series

On August 18, 2025, Colton Brown-Underwood co-hosted alongside Kaitlyn Bristowe on a dating reality series titled, Are You My First? Featuring twenty-one virgin singles that premiered on Hulu.

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