Never able to establish himself as an everyday player for a full season, Cummings’ skills as a pinch hitter and fielder kept him in the major leagues. After breaking in with the Pittsburgh Pirates in 1993, Cummings played more than 100 games in a season only once, in 1997, when he split time with the Pirates and the Philadelphia Phillies. In 63 games leading off for the Phillies he hit .303, earning regular playing time for the second half of the season. His impatience at the plate ruined his on-base percentage in 1998, and he spent the remainder of his career as a fourth or fifth outfielder.
A free agent after spending 2000 with the Boston Red Sox and Minnesota Twins, Cummings signed a minor-league deal with the Arizona Diamondbacks in 2001. Garnering only two hits and no runs in his seven at-bats, Cummings was reassigned to Triple-A Tucson to make room for reliever Troy Brohawn. When the rosters expanded in September he returned to the team and played in 14 games, primarily as a defensive replacement.