Kipkemoi first began competing at road events in Kenya and ran a time of 62:59 minutes at the 2009 Nairobi Half Marathon. He was chosen for the Kenyan team at the 2011 All-Africa Games and was the silver medallist in the half marathon behind Lelisa Desisa, as well as fourth in the 10,000 m. That October, he came second at the Valencia Half Marathon, improving his personal best to 59:47 minutes.