Kipyego's first major international competition was the 2014 IAAF World Junior Championships in Eugene, Oregon, where he won the world junior steeplechase title in a time of 8:25.57.[2] His countryman Titus Kibiego led early in the race, but with one lap to go Kipyego took the lead and he had the best final two barriers to win with a final-lap time of 61.21 seconds.[2]
Kipyego was a regular participant in Diamond League steeplechase races over the next several years. He was ranked 10th in the LetsRun.com 2016 year-end rankings, where it was noted that in any other country Kipyego would be a top-tier prospect, but he was overshadowed due to the Kenyan dominance in the steeplechase at the time.[3] Due to this steep national level competition, Kipyego never made a World or Olympic team for his country.
On 8 September 2024, Kipyego finished the Münster Marathon in a time of 02:14:48 h.[4]
