On September 24, 1999, a 33-year-old Orlando Canizales (50-4-1, 37 KOs) and Frank Toledo met in the ring.
Canizales came in to the fight on a 1-fight win streak with a 67% KO rate, and was fighting after a gap of 3 months and 20 days.
Orlando Canizales lost to Frank Toledo via split decision in the 10-round fight, and adds an loss to his record at 50-5-1.
On December 11, 1998, a 33-year-old Orlando Canizales (49-3-1, 36 KOs) and Richard De Jesus met in the ring.
Canizales came in to the fight on a 7-fight win streak with a 67% KO rate, and was fighting after a gap of 1 month and 19 days.
Orlando Canizales lost to Richard De Jesus via majority decision in the 10-round fight, and adds an loss to his record at 49-4-1.
On March 23, 1996, a 30-year-old Orlando Canizales (42-2-1, 31 KOs) and a 25-year-old Junior Jones (39-2, 25 KOs) met in the ring.
Canizales came in to the fight on a 4-fight win streak with a 68% KO rate, and was fighting after a gap of 4 months and 19 days. Jones was on a 6-fight win streak with a 61% KO rate, and fighting after a layoff of 2 months and 11 days.
Junior Jones defeated Orlando Canizales via split decision in the 12-round super-bantamweight fight. Jones improves his record to 40-2, while Canizales adds a loss to his record at 42-3-1.
On January 7, 1995, a 29-year-old Orlando Canizales (38-1-1, 28 KOs) got a shot at the super-bantamweight WBA title held by 34-year-old Puerto Rican boxer Wilfredo Vazquez (41-6-2, 32 KOs).
Canizales came in to the fight on a 27-fight win streak with a 70% KO rate, and was fighting after a gap of 2 months and 23 days. Vázquez was on a 13-fight win streak with a 65% KO rate, and fighting after a layoff of 2 months and 25 days.
Wilfredo Vázquez defeated Orlando Canizales via split decision and successfully defended his WBA super-bantamweight title. Vázquez improves his record to 42-6-2, while Canizales adds a loss to his record at 38-2-1.
On July 20, 1986, a 20-year-old Orlando Canizales (11-0-1, 9 KOs) and Paul Gonzales met in the ring in a flyweight bout.
Canizales came in to the fight on a 9-fight win streak with a 75% KO rate, and was fighting after a gap of 2 months and 14 days.
Orlando Canizales lost to Paul Gonzales via unanimous decision in the 12-round flyweight fight, and adds an loss to his record at 11-1-1.