Toccara Montgomery is considered one of the most dominant female wrestlers in United States history.

In her first Senior World Championships appearance in 2001, she captured a silver medal.

Still a senior in high school, Montgomery won seven gold medals at major Senior women’s events while also claiming a silver medal at the Junior World Championships in 2001.

She was named International Women’s Wrestler of the Year by FILA in 2001, becoming the first American female and only the third American ever to win the prestigious award. Montgomery joined fellow Distinguished Members John Smith (1995) and Stephen Neal (1999) as Americans to win the FILA International Wrestler of the Year award. She was also named the TheMat.com/ASICS Girls High School Wrestler of the Year in 2001.

Montgomery returned to the World Championships in 2002 and 2003. She repeated as a silver medalist in 2003.

She made history in 2004 as the first Black woman to wrestle for the U.S. in the Olympics, finishing seventh.

Montgomery was a four-time United States Open champion and the Pan American Games champion in 2002 and 2003. She was a United States Girls Wrestling Association national champion and a three-time finalist.

Montgomery began her career at East Technical High School in Cleveland, as not only one of the first members of the school’s wrestling team, but also one of the first girls to compete in a male-dominated sport on the prep level.

She was a national champion as a senior for East Tech after a runner-up finish as a junior.

Montgomery was a two-time national champion for the University of the Cumberlands, winning the first two college national championships ever held for women’s wrestling.

She was inducted into the Cumberlands Athletic Hall of Fame in 2006 and into the Ohio High School Wrestling Coaches Association Hall of Fame in 2023, becoming the first female honored by the organization.

The Ohio High School Athletic Association’s Female Wrestler of the Year award is named in her honor.

She became the first female to serve as head coach for a women’s college wrestling team when she was named head coach at Lindenwood University in 2010. Montgomery began her coaching career as a graduate assistant at Cumberlands in 2006.

Currently she works as an assistant principal for the St. Louis Public School District while also serving also the head girls wrestling coach for Clayton High School and an assistant coach with the St. Louis Warriors youth wrestling club.