During his playing career, Riggleman was an infielder and outfielder in the Los Angeles Dodgers and St. Louis Cardinals minor league systems from 1974 to 1981.

[6] During the 1976 season, Riggleman transferred to the St. Louis Cardinals, where he was assigned to the double-A Arkansas Travelers and played in both infield and outfield.

In 1998, Riggleman's Cubs earned a wild card postseason appearance that ultimately resulted in a loss to the Atlanta Braves in the National League Division Series.

[7] Riggleman spent the period from 2001 to 2004 as bench coach for the Los Angeles Dodgers under manager Jim Tracy.

Riggleman began the 2008 season as the bench coach for the Seattle Mariners under new manager John McLaren.

[7] Riggleman was named bench coach for the Washington Nationals for the 2009 season, and was promoted to interim manager on July 12, 2009, following Manny Acta's midseason dismissal.

Riggleman hired Burton Rocks as his agent to negotiate his managerial deal with the Washington Nationals in November 2009.

[14] On December 12, 2012, Riggleman was promoted to manage the Reds' Class AAA team, the Louisville Bats, in 2013.