In 2011, Cheever was named the U.S. Snowboarding Champion, and took 2nd-place, twice, in the FIS World Cup at Stoneham Mountain Resort in Quebec and Chiesa in Valmalenco in Italy, becoming the second American male ever in his discipline to win the World Cup.
Cheever and teammate, Mick Dierdorf, placed 2nd at the Team Snowboard Cross (BXT) FIS World Cup in Veysonnaz, Switzerland, March 2017.
During Thanksgiving of 1997, his parents enrolled him in free snowboarding lessons at Attitash Bear Peak, in neighboring New Hampshire.
He has pre-qualified 1st at US Open Slope Style and has won many freestyle and free ride competitions.
In February 2010, Cheever fractured his right ankle, while attempting double corks, on a trampoline at the USSA Center of Excellence.