Among his first successes on the road was a win at the Grand Prix von Bern 10-miler in 2002. He won the Paris Marathon in 2005 with a time of 2:08:02. Kipsang was the 2006 winner of the 20 van Alphen race. He finished third at the 2007 Berlin Marathon, setting a personal best of 2:07:29 hours, and won the 2009 Tokyo Marathon. He returned to Tokyo in both 2010 and 2011 but managed only ninth and eighth place, respectively. He returned to the marathon podium in Japan at the inaugural edition of the Osaka Marathon in October 2011, placing third in a time of 2:14:18 hours.