Bobby Simmons (born June 2, 1980) is an American former professional basketball player. He last played for the Los Angeles Clippers of the National Basketball Association (NBA). He won the NBA Most Improved Player Award in 2005.

After graduating from Chicago's Neal F. Simeon High School, Simmons played three years of college basketball for DePaul University. During his three seasons at DePaul, Simmons averaged 13.6 points per game, 7.5 rebounds per game and 2.2 assists per game.

Simmons was selected in the second round (41st pick overall) of the 2001 NBA draft by the Seattle SuperSonics. Simmons's draft rights were traded to the Washington Wizards for Predrag Drobnjak on June 27, 2001.

Simmons was traded by the Wizards on September 11, 2002, shortly before the start of the 2002–03 NBA season, to the Detroit Pistons with Hubert Davis and Richard Hamilton for Jerry Stackhouse, Brian Cardinal, and Ratko Varda. He was released by the Pistons on September 24 and, less than two weeks later, signed with the Wizards again on October 10. Later, Simmons signed a free-agent contract with the Los Angeles Clippers on September 26, 2003.

The 6'8", 235 lb small forward had a breakout year during the 2004–05 NBA season with the Los Angeles Clippers in which he averaged a career-high 16.4 points per game. He was rewarded for his stellar play with the NBA Most Improved Player Award.