During his freshman year Grapevine Faith won the TAPPS Division 2 Texas state championship in boys' soccer.

Cannon won back-to-back national championships for FC Dallas's academy before joining University of California, Los Angeles.

[2] Cannon played one year of college soccer at the University of California, Los Angeles in 2016, making 20 appearances for the Bruins.

[5] Cannon made his MLS debut for the club on September 2, in a 2–2 tie at home to the New York Red Bulls, as an added-time substitute for Michael Barrios.

[7] His team did not take part in the subsequent season restart, MLS is Back Tournament, being forced to withdraw after ten players and one staff member tested positive for coronavirus.

[18] On September 26, 2023, Cannon officially joined English club Queens Park Rangers on a free transfer, signing a four-year deal.

On October 16, 2018, Cannon made his first senior appearance for the United States men's national soccer team in a friendly against Peru, which finished 1–1.

[20] He made the cut for the 2019 CONCACAF Gold Cup, due to Tyler Adams's injury,[21] and played four matches including the 1–0 final loss to Mexico.

[23][24] On June 6, 2021, he came on as a substitute for the former for the second half of extra time, as the United States defeated Mexico 3–2 in the CONCACAF Nations League final.

[26] He made four appearances at the 2021 CONCACAF Gold Cup, as second-choice to Shaq Moore and starting only in the 1–0 win over Mexico in the final on August 1.