In 2017, Simmons signed his first professional contract with Swedish
Allsvenskan side
Dalkurd FF. In November 2017, he was loaned to Finnish
Kakkonen side
Mikkelin Palloilijat. In January 2019, he signed with
HFX Wanderers FC of the
Canadian Premier League. He had had other offers to remain in Europe, but chose to return to Canada, intrigued by the opportunity to play in the league's inaugural season. At the end of the season, he departed the club. In November 2019, he went on trial with Swedish club
GAIS. In February 2020, he signed with
Cavalry FC. In November 2020, Simmons re-signed with the club for the 2021 season and also spent the offseason training with Swedish
Allsvenskan club
Östersunds FK. On June 30, 2021, he scored his first professional goal in a match against
Atlético Ottawa. In January 2022, it was announced Simmons would return for the 2022 season, his third with the club. In December 2022, he signed with
Vancouver FC ahead of the 2023 season. In January 2023, Simmons joined
Championship club
Huddersfield Town on a training stint. In September 2023, he was named to the CPL Team of the Week for the first time. After the season, he went on a training stint with English
National League side
Barnet, as well as another club in the same league. In May 2024, he departed the club by mutual consent. In June 2024, Simmons joined English
National League side
Wealdstone. In August 2024, he went on loan to
Bedford Town in the seventh tier
Southern Football League Premier Central. In January 2025, he agreed to a mutual termination of his contract with Wealdstone and joined Bedford Town on a permanent basis. He helped the team win the league title in 2024-25, earning promotion to the
National League North. In September 2025, he returned to the Southern League Premier Division Central, joining rivals
Real Bedford. ==International career==