Kelly was a member of four playoff teams in his career, having helped the Dodgers win the 1995 NL West Division, the Mariners win the 1997 AL West, and the Rangers win the 1998 and 1999 AL Western Division. (Kelly played ten games for the 2000 American League East-winning New York Yankees, but played his final game on April 18, long before the playoffs.)
In 14 seasons, he played in 1,337 games and had 4,797 at bats, 687 runs, 1,390 hits, 241 doubles, 30 triples, 124 home runs, 585 RBI, 235 stolen bases, 317 walks, a .290 batting average, a .337 on-base percentage and a .430 slugging percentage.
On November 16, 2007, Kelly was hired as the San Francisco Giants new first base coach and hitting instructor. As a manager of the Augusta GreenJackets, he gained a reputation for his aggressive approach to baserunning. In February 2008, he told Giants pitchers that he didn't want them to use the fact that they were pitchers as an excuse for poor baserunning.
Kelly has five sons Roberto Kelly Jr. is a college football player at Valparaiso University and Xavier Kelly is a state-ranked wrestler in Florida. and three daughters: Charlene Kelly, Rhianna Kelly, Bianca Kelly.