Chala Regasa began his professional running career focusing on shorter road distances. In 2019, he won the 10K Valencia Ibercaja with a personal best time of 27:23. That same year, he also served as a pacemaker for
Eliud Kipchoge during his historic sub-2-hour marathon attempt (INEOS 1:59 Challenge) in Vienna. In 2022, Regasa achieved a personal best in the half marathon, running 59:10 to finish second at the eDreams Mitja Marató de Barcelona. Regasa made his full marathon debut in 2023, where he finished fifth at the
Rotterdam Marathon with a time of 2:06:11. In the 2024 marathon season, Regasa won the
Vienna City Marathon in April with a time of 2:06:35. In December, he became the first Ethiopian man to win the
Abu Dhabi Marathon, crossing the line in 2:06:16. In April 2025, Regasa further improved his marathon personal best at the
Rotterdam Marathon, finishing second in 2:05:06. == Personal bests ==