Born and raised in tiny Keewatin in northern Minnesota, Cappelletti played college football at the University of Minnesota, where he was a quarterback, backing up All-AmericanPaul Giel. Cappelletti kicked extra points, but the Golden Gophers did not kick field goals in those years. However, as a sophomore in 1952, Cappelletti talked the coach into letting him try a game-winning 43-yard kick against Iowa. As a senior in 1954, Cappelletti switched to T-quarterback and led Minnesota to a 7–2 record, missing the final game with an elbow injury, a 27–0 loss at Wisconsin. He was named to the All-Big Ten second team, but was not selected in the 1955 NFL draft.
Cappelletti was out of pro football in 1959, back in Minnesota. With the launch of the American Football League in 1960, he joined the Boston Patriots and was initially a kicker and defensive back. He switched to offense late in that season and teamed up with quarterback Babe Parilli to form a tandem nicknamed "Grand Opera Twins", due to their Italian surnames. Cappelletti won AFL MVP honors in 1964, led the league in scoring five times and was a five-time AFL All-Star. He holds the professional football record for points over a six-year period, points over an 11-year period and percentage of his team's total points over an eight-year period. One of 20 AFL players active during the entirety of the league's ten-year existence, Cappelletti was also among just three players who played in every one of his team's AFL games. He played with the Patriots all 11 years in Boston, from 1960 through the 1970 NFL merger season, and retired in late August 1971 at age 37; he was the AFL's all-time leading scorer with 1,130 points and among the AFL's top ten all-time receivers in yards and in receptions. Cappelletti had two of the top five scoring seasons in pro football history, with 155 points in 1964 and 147 points in 1961. His Patriots team scoring record lasted until it was broken by Adam Vinatieri on December 5, 2005. To date, as of the end of the 2017 season, Cappelletti is the Patriots' 11th all-time leading receiver in receptions with 292 catches and 9th in receiving yards with 4,589 yards. He is 5th in Patriots history in receiving touchdowns with 42 and has the most field goal attempts in team history. During Cappelletti's pro career, he also returned punts and kickoffs, played defensive back and even had one pass completion for a touchdown. Cappelletti was just the second AFL player to record three interceptions in a regular-season game, holds the professional football record for most touchdowns in Saturday games, scored 18 points or more in a game ten times and scored 20 or more points in a game eight times. He set the AFL single-game record by scoring 28 points in the Patriots' 42–14 rout of Houston on December 18, 1965. Cappelletti is the only player in professional football history to run for a two-point conversion, throw for a two-point conversion, catch a pass, intercept a pass, return a punt and return a kickoff in the same season. He kicked six field goals in a 39–10 win at Denver on October 4, 1964, and became one of only two AFL kickers with at least four field goals per game for three consecutive games. Cappelletti kicked the longest field goal in the AFL in consecutive seasons and led the AFL in field-goal percentage in 1965. In 1984, Cappelletti was inducted into the National Italian American Sports Hall of Fame. However, he has not been selected to the Pro Football Hall of Fame. In 2003, he was named to the Professional Football Researchers Association Hall of Very Good in the association's inaugural HOVG class.
Broadcasting
Cappelletti worked alongside Gil Santos as a color commentator for the Patriots' radio broadcasts on the New England Patriots Radio Network. The Santos-Cappelletti duo lasted 28 seasons, the longest radio tandem in modern NFL history. They called 585 regular-season and postseason games together, including a league-record six Super Bowls. Cappelletti also served as color commentator for the Boston College Eagles during the famous "Hail Flutie" game in 1984. Cappelletti can be heard supporting Dan Davis' now-famous call by yelling "He got it!, He got it!, I don't believe it!" On July 20, 2012, Cappelletti announced his retirement from broadcasting.