Cunningham attended Terrebonne High School, where he competed in football, baseball, tennis and track.
Although he had an excellent preseason, including a game-winning field goal against the Baltimore Ravens, the team released him on August 19 and decided to keep veteran Chris Jacke.
[3][4] On April 15, 1997, he was signed by the Dallas Cowboys to compete for the starting job, after Chris Boniol left in free agency.
In 1999, he was limited with a sprained right ankle and was released 12 games into the season, after he slumped and made only 12-of-22 of his field goal attempts (54.5%).
[7] On December 14, 1999, he signed as a free agent with the Carolina Panthers, to replace an injured John Kasay.
[8] On December 18, he tied a franchise single-game record by making 5 extra points against the San Francisco 49ers.
[9] On March 16, 2001, he signed a two-year contract with the Cincinnati Bengals, to compete in training camp with Neil Rackers.
[11] On November 27, 2002, he was signed as a free agent by the Jacksonville Jaguars, to replace a struggling Tim Seder.
[15] Cunningham also received some notoriety during his NFL career for sharing the same name of the Happy Days television character played by Ron Howard.