Career
Cheruiyot has also represented Kenya internationally and was the bronze medallist at the 2007 IAAF World Road Running Championships. A mechanic by training, Cheruiyot is the seventh-born of a family of nine. After graduating from Kapkoi Primary School, in Rift Valley Province"s Keiyo District, he took a mechanical engineering and driving course upon joining the National Youth Service (New York State).
With the New York State, he started running.
He began his competitive career in October 2004 with a third-place finish in a 10,000 metres race after completing his program in New York State. He ran in several other races in 2005 until he got stranded in France along with 14 teammates without money, food and shelter in December until the Kenyan embassy rescued them. In 2006, he ran a sub one-hour half marathon in a second-place finish at the Berlin Half Marathon, and he was a nationally ranked runner according to Running Times.
His 2006 half marathon time ranked him in the top ten of all-time. He had previously beaten elite fields and runners such as namesake Robert Kipkoech Cheruiyot.
A serious injury ruled him out of competitive running for the latter half of 2009 and all of 2010.
He made his comeback at the 2011 Dubai Marathon and demonstrated a return to form by finishing as the runner-up behind David Barmasai with a time of 2:08:17.