He began taking part in road races in 2008, and he ran a time of 1:02:43 at the Nairobi Half Marathon for third place. He entered the Berlin Half Marathon the following year and improved his time to 1:01:26, finishing in twelfth place. In September 2009, he ran at the Rotterdam Half Marathon but was three minutes behind the winner Sammy Kitwara, having run 1:02:00 for fourteenth place. He stepped up to make his marathon debut at the 2009 Amsterdam Marathon and scored his first major victory. In one of the fastest ever debuts, he ran a time of 2:06:18 to break Haile Gebrselassie's four-year-old course record.
He ran at the 20 van Alphen in March 2010 and finished in third place, behind Bernard Chepkok and Dejene Yirdaw, but recorded a 20 km best time of 58:56. He came 22nd at the 2010 Boston Marathon and fared better at the 2010 Berlin Marathon, taking eighth place in 2:10:34 hours. He did not compete in 2011 but returned to competition at the 2012 Vienna Marathon with a runner-up performance in 2:07:38 hours.
- All results regarding marathon, unless stated otherwise
|2009||Amsterdam Marathon||Amsterdam, Netherlands||1st||2:06:18|
|2010||Boston Marathon||Boston, United States||22nd||2:21:12|
|2012||Vienna Marathon||Vienna, Austria||2nd||2:07:38|
|10 km||28:18||Rotterdam, Netherlands||13 September 2009|
|20 km||58:56||Alphen aan den Rijn, Netherlands||7 March 2010|
|Half marathon||1:01:26||Berlin, Germany||5 April 2009|
|Marathon||2:06:18||Amsterdam, Netherlands||18 October 2009|
- All information taken from IAAF profile.
- 2008 Nairobi Half Marathon – 3rd
- Gilbert Yegon. Volare Sports. Retrieved on 2010-04-30.
- Wenig, Jörg (2009-04-05). In debut, Kipyego takes Berlin Half Marathon in 59:34. IAAF. Retrieved on 2010-04-30.
- van Hemert, Wim (2009-09-13). Kitwara blazes 58:58 in Rotterdam. IAAF. Retrieved on 2010-04-30.
- van Hemert, Wim (2009-10-18). Another sizzling debut - 2:06:18 by Yegon in Amsterdam to break Gebrselassie's course record. IAAF. Retrieved on 2010-04-30.
- Keniaan Chepkok wint 20 van Alphen (Dutch). NuSport (2010-03-07). Retrieved on 2010-04-30.
- Wenig, Jorg (2012-04-15). Sugut runs 2:06:58 while Tola defends; Haile beats Paula in chase in Vienna. IAAF. Retrieved on 2012-04-21.