Darrion Caldwell has seven losses against six opponents on his MMA record. For a list of Caldwell's best fights, refer to "Best fights of Darrion Caldwell".
On February 4, 2023 Darrion Caldwell faced off against Nikita Mikhailov in a bantamweight bout at age 35. He was coming in with a record of 15-7 (7). Caldwell lost the fight via 3-round unanimous decision.
On January 29, 2022 Darrion Caldwell faced off against Enrique Barzola in a bantamweight bout at age 34. He was coming in with a record of 15-6 (7), and Barzola was 32 years old and with a record of 16-5-2 (8). Caldwell lost the fight via 3rd-round TKO.
On May 21, 2021 Darrion Caldwell faced off against Leandro Higo in a bantamweight bout at age 33. He was coming in with a record of 15-5 (7), and Higo was 32 years old and with a record of 20-5 (14). Caldwell lost the fight via 3-round split decision.
On November 19, 2020 Darrion Caldwell faced off against A. J. McKee in a featherweight bout at age 32. He was coming in with a record of 15-4 (7), and McKee was 25 years old and with a record of 16-0 (10). Caldwell lost the fight via 1st-round submission.
On June 14, 2019 Darrion Caldwell met Kyoji Horiguchi in a bantamweight (Bellator World Championship) title defense fight. Caldwell was 31 years old and with a record of 13-3 (6), and Horiguchi was 28 years old and with a record of 27-2 (17). Caldwell lost the fight via 5-round unanimous decision and lost the title.
On December 31, 2018 Darrion Caldwell fought Kyoji Horiguchi in a bantamweight title fight for Horiguchi's Rizin Championship title. Caldwell was 31 years old and with a record of 13-2 (6), and Horiguchi was 28 years old and with a record of 25-2 (15). Caldwell lost the fight via 3rd-round submission.
On July 22, 2016 Darrion Caldwell faced off against Joe Taimanglo in a bantamweight bout at age 28. He was coming in with a record of 9-1 (4), and Taimanglo was 32 years old and with a record of 22-6-1 (16). Caldwell lost the fight via 3rd-round submission.
