Diego Corrales, nicknamed "Chico", was born in Columbia, South Carolina and moved around the country with his teenage mother Olga. He was three years old when Olga found a permanent home in Sacramento and then meeting her soon to be husband Ray Woods. Growing up in the Oak Park area, Diego was a feisty boy who was very talkative and personable, Chico wasn't afraid to try anything, including boxing.

He became interested in boxing at four years old, and with the help of Ray, he quickly developed good skills. He tried other sports and participated in football and track and field but was too small. At age 10 he began going to the Police Athletic League Gm and he quickly flourished under Ray's guidance. Finding an individual sport suited Diego just find as he could garnish all the attention.

He had his first amateur fight at age 11 and it was evident he had superior skills for a boy his age.

Despite a rough childhood which included getting into a lot of trouble, Diego was forced to turn into a man as a teenager. He began training at the Washington Neighborhood Center unter the direction of Don Connolly. He began to thrive and was developing into a top amateur fighter. As an amateur, Diego compiled a record of 105-12 and took second place at the U.S. Amateur Championships and was a bronze medalist in the 1995 Pan American Games.

Rated by many as one of the greatest bouts of all time was his May 7th, 2005 10th round knockout victory over Jose Luis Castillo for the The World Lightweight Championship. Though Corrales twice came off the canvas to knock Castillo out, in the same round, that result is tempered by the fact that after each knockdown, Corrales, while on his feet, intentionally spit his mouth piece out. On both occasions the referee had to halt the action, however brief, to put Corrales' mouthpiece back in and order points deducted from Corrales' scorecard, giving Corrales additional time to recover before scoring his improbable knockout.

The two men just kept trading heavy punches, round after round, but neither man went down. It immediately became clear to the spectators that this was going to be a great fight, but few knew just how great it'd be.

Early in the 10th round, Castillo landed a clean punch that knocked Corrales down. The referee gave him a 10-count, and Corrales was back in action after the referee counted to eight. Then, Castillo immediately landed another clean shot that knocked Corrales down again. Things were looking grim for Corrales, and after counting to nine, Corrales was ready to fight again.