Greenwald began calling games for the Giants in 1979, but ended this stint in 1986, after Greenwald had a disagreement with station management. After joining the New York Yankees radio broadcast team for the next two seasons, Greenwald returned to the Giants in 1989 when the team reached the World Series. Greenwald later expressed resentment toward Yankees owner George Steinbrenner, saying "Steinbrenner is everything you've heard, maybe worse." He remained in San Francisco until 1996, when he announced his retirement. At the time he retired, Greenwald had announced 2,798 consecutive games. In his book This Copyrighted Broadcast, Greenwald cites disagreements with Giants' Vice PresidentLarry Baer as his reason for retiring. The Giants hired former Baltimore Orioles and ESPN announcer Jon Miller as Greenwald's replacement. Perhaps Hank Greenwald's most memorable call was his emotional description of the final out in Game 5 of the 1989 National League Championship Series. This came after Greenwald called Giants first baseman Will Clark's pennant clinching hit off of Chicago Cubsrelief pitcherMitch Williams in the bottom of the eighth inning:
In 1997, Greenwald was employed by the CBS Radio network as a baseball announcer, calling Saturday Game of the Week broadcasts as well as the NLDS between the Giants and Florida Marlins.
In 2004, Greenwald was hired as a television play-by-play announcer for the Oakland Athletics working about 1/3 of the team's telecasts with analyst Ray Fosse. He announced games for the A's in the 2004 and 2005 seasons.
His son Doug, named after General Douglas MacArthur, is the play-by-play announcer for the Fresno Grizzlies, formerly the Giants' AAA affiliate and now the Houston Astros' affiliate. He also has announced baseball and women's basketball for the Santa Clara Broncos. His first game announcing for the major league Giants was on September 6, 2009; he filled in for regular announcer Dave Flemming, whose wife was expected to give birth. Most recently, he also had to fill in for both Flemming and fellow broadcaster Jon Miller during a July 23–25, 2010 series against the Arizona Diamondbacks since Miller had to go up to Cooperstown to receive the Ford C. Frick Award, and Flemming also had to be there to support him after Flemming solely called the first game on July 22. Like Flemming, Doug solely called the remaining three games on the radio accompanied by color commentator J. T. Snow. Greenwald called the play-by-play alongside Randy Winn for the San Francisco Giants game on the June 14, 2015 broadcast on KNBR.