Diggs was nominated by the Image Awards for Outstanding Actor in a Motion Picture for his role in The Best Man in 2000 and in 2002 for Outstanding Supporting Actor in a Comedy Series for his role Ally McBeal. He won the Screen Actors Guild Award for Outstanding Performace by a Cast in a Motion Picture in 2003 for his role in Chicago. He also was nominated for an Image Award for outstanding Actor in a Motion Picture for his role in Brown Sugar. He won the Image Award for Outstanding Actor in a Drama for his role in Kevin Hill in 2005. He was also nominated in 2008 and won in 2009 the Image Award for Ooutstanding Supporting Actor in a Drama Series for his role in Private Practice. He also was nominated in 2010 from the Image Awards, the Outstanding Actor in a Drama Series for Private Practice.