Kitwara, a policeman by occupation, won the 2009 Rotterdam Half Marathon in a time of 58:58 – a course record which made him only the sixth runner to complete a sub-59-minute run. Earlier in the year Kitwara won another major half marathon, the City-Pier-City half marathon in The Hague, beating Haile Gebrselassie into second place, as well as winning at the Peachtree Road Race. He set a new course record of 27:25.6 at the World's Best 10K in February that year. Kitwara won the 10,000 m race at the Kenyan Trials in June 2009, earning a place in the national team for the 2009 World Championships in Berlin. However, he was subsequently removed from the team by Athletics Kenya for participating in road races after the Trials. He did, however compete at the 2009 IAAF World Half Marathon Championships in Birmingham, finishing 10th.