[1] Cheprot first emerged as a distance runner on the American road circuit in 2009, winning a series of low level races.

[3][4] Cheprot made a breakthrough at the 2013 Roma-Ostia Half Marathon, finishing third behind world champion Wilson Kiprop with a time of 59:20 minutes.

[2] A fourth-place finish at the 2014 Roma-Ostia earned him his first international call-up and at the 2014 IAAF World Half Marathon Championships he placed 22nd overall.

[4] He also managed a 10K best at the Prague Grand Prix that year, recording a time of 27:41 minutes which again ranked him in the world's top ten for the season.

[10] He was chosen for the Kenyan team at the 2016 IAAF World Half Marathon Championships and earned his first global medal as his sixth-place finish helped the Kenyan trio of Cheprot, Geoffrey Kipsang Kamworor and Bedan Karoki Muchiri to record a sub-3-hour time for the team gold medals.