Dowling attended St. Ignatius High School, located in Cleveland, Ohio, where he was a multi-sport standout.
As a senior in 1964, he avenged that loss against Benedictine in the same City Championship Charity Game in a 48–6 rout, passing for 4 touchdowns and running for a 71-yard score.
In basketball, he led the team to a City title by making 4 free throws in the championship game's last 34 seconds to help turn a 13-point deficit into a 53–50 victory.
He led the team to an Ivy League championship, which included a 24-20 come-from-behind victory over Harvard University, with a 66-yard touchdown pass in the last 2:16 minutes of the game.
Harvard, trailing 29–13 with 42 seconds remaining, rallied to tie the game, while Dowling stood helplessly on the sideline.
[16] On November 14, he was signed by the Green Bay Packers to provide depth after starter Lynn Dickey suffered a broken leg.
[18] On July 10, 1978, he was signed by the Los Angeles Rams, reuniting with George Allen who was also his head coach with the Redskins.
[20] Dowling was a member of the Delta Kappa Epsilon fraternity and the Skull and Bones Society.
The character B.D., in the Doonesbury comic strip, was originally based on and named after Dowling, a Yale classmate of cartoonist Garry Trudeau.
[21] In 1969, he appeared on The Dating Game television show with former Harvard quarterback Frank Champi.
[22] He was involved with the Ivy Satellite Network, which specialized in closed-circuit telecasts of sport games between smaller colleges.
[23] Dowling was an insurance industry consultant and worked with a venture capitalist in the Boston area.