Early life and career
Stockton was born in Philadelphia, Pennsylvania. He attended Forest Hills High School in Queens, New York, graduating in 1960. He went on to college at Syracuse University, where he received his degree in political science in 1964. In 1965, he began his sportscasting career at local radio and television stations in Philadelphia. He became sports director at KDKA-TV in Pittsburgh in 1967, and moved to WBZ-TV and WBZ radio in Boston in 1971. Three years later, he began calling Boston Celtics telecasts for WBZ, and the following year he became the lead announcer for Boston Red Sox games on WSBK-TV. Stockton was part of the broadcast crew for NBC Sports' coverage of the 1975 World Series, and on television called Carlton Fisk's famous, game-winning home run in Game 6 of that series. In 2001, he was inducted as a broadcaster into the Naismith Basketball Hall of Fame. Stockton has been named as one of the top 50 network sportscasters of all time.
Stockton started freelancing for CBS Sports in the late 1960s, while still doing local television in Pittsburgh. In 1978 (following a two-year stint calling NFL games for NBC), he joined CBS full-time, and from then until 1994 covered a variety of sports for that network, including the NFL, the NBA (for which Stockton was the lead play-by-play man from 1981 to 1990), Major League Baseball (with Jim Kaat from 1990 to 1992. Stockton was the number #2 play-by-play man behind Jack Buck and Sean McDonough in 1992.), college basketball including ten years as a play-by-play broadcaster of the NCAA Regional Finals. Stockton also was the host at the famous upset of Villanova over Georgetown in 1985.
In addition, he was the host of the Pan American Games in San Juan in 1979, and covered swimming and diving at the Pan American Games in Edmonton and Caracas. Stockton also broadcast the World Swimming and Diving Championships in Guayaquil, Ecuador, the World Basketball Championships in Cali, Colombia, and the World Figure Skating Championships in Helsinki in the first year that CBS acquired the rights. When CBS began covering the Winter Olympics, Stockton was assigned to cover speed skating in France in 1992 and two years later, he called the speed skating events in the 1994 Norway Games including Dan Jansen's record-breaking triumph of the 1000 meter gold medal as well as the gold medal victories of Bonnie Blair.
Stockton left CBS in 1994 for Fox Sports, which continues to employ him on NFL and Major League Baseball telecasts. From the time he was hired until 2006, he was Fox's second-team announcer for NFL games (behind Pat Summerall and later, Joe Buck), working alongside Matt Millen then Troy Aikman, Daryl Johnston, and Tony Siragusa. For Fox's MLB coverage, he has worked with Eric Karros, Joe Girardi, Mark Grace and Tim McCarver. He currently works with Kirk Morrison, Brady Quinn, and Donovan McNabb for football and Brevin Knight for Fox College Hoops.
Since 1995, Stockton has called NBA telecasts for Turner's TNT channel. Since 2007, Stockton has called postseason Major League Baseball games on TBS. That year, he partnered with Ron Darling to call the National League Division Series for the network. In 2008, he called the AL Central tiebreaker game with Darling and Harold Reynolds, followed by the NLDS with Darling and Tony Gwynn. In 2009, he teamed with Bob Brenly to call the NLDS for TBS, and the two have worked together for the NLDS every year since until 2014, when TBS began carring only two LDS, rotating between AL/NL each year. TBS and Fox began splitting the LDS from 2014 on. TBS was previously the exclusive home of the LDS from 2007 to 2013. Stockton split play-by-play duties during the 2010 regular season on TBS with NBA on TNT studio host Ernie Johnson, Jr. and Milwaukee Brewers announcer Brian Anderson. In 2011, he partnered with Ron Darling and John Smoltz to call game 5 of National League Division Series between the St. Louis Cardinals and Philadelphia Phillies for TBS as his normal partner Brenly was away at a family event.
From 1993 to 1995, Stockton also called local TV broadcasts of the Oakland Athletics. In 2004, he began doing part-time local television work for the San Antonio Spurs. Stockton commentated on Super Bowl XXXVIII alongside Daryl Johnston and Super Bowl XLII alongside Sterling Sharpe on the international feed, provided by the NFL Network. This is the feed used by the BBC and certain other English-language broadcasters outside North America. Starting in 2010, Dick assumed play-by-play duties for Miami Dolphins preseason games on WFOR; he substituted for Jimmy Cefalo as play-by-play on the Dolphins' radio call of the team's Monday Night Football game against the New England Patriots on October 4, 2010.
Stockton provides the play-by-play commentary for NFL Fever 2000 alongside Matt Millen.
For one season in 1972, he and Ken Coleman, fellow Boston Red Sox broadcaster, alternated play-by-play duties with Coleman as the secondary play-by-play announcer and with Stockton as main play-by-play announcer with no color commentators.
Stockton is married to Jamie Drinkwater. The couple were married July 31, 2014 at her family's home in New York, on the St. Lawrence River. The couple will divide their time between homes in Boca Raton, Florida and Carefree, Arizona. Stockton's previous marriage to sportscaster Lesley Visser ended in divorce in 2010.
- 1974–1975: Boston Celtics TV play-by-play (WBZ-TV)
- 1975–1976: New York Knicks TV play-by-play (WOR-TV)
- 1975–1978: Boston Red Sox TV play-by-play (WSBK-TV)
- 1976–1977: NFL on NBC play-by-play
- 1978–1993: NFL on CBS play-by-play
- 1981–1990: NBA on CBS lead play-by-play
- 1990–1992: Major League Baseball on CBS #2 play-by-play
- 1992–1994: Olympics on CBS announcer
- 1993–1995: Oakland Athletics TV play-by-play (KRON-TV)
- 1994–present: NFL on Fox play-by-play
- 1995–present: NBA on TNT play-by-play
- 1995: NHL on Fox play-by-play
- 2003–present: Major League Baseball on Fox play-by-play 
- 2004–present: San Antonio Spurs TV play-by-play (part-time)
- 2007–2013: Major League Baseball on TBS Division Series play-by-play, lead play-by-play
- 2010–present: Miami Dolphins Preseason TV play-by-play
- 2010: BCS on Fox Orange Bowl play-by-play
- 2013–present: College Football on Fox fill-in play-by-play
- 2013–present: Fox College Hoops play-by-play