In 2006 he earned seventh place in the New York City Marathon. Kipsang did not compete in the marathon for two years between 2008 and 2010, and his comeback at the Seoul International Marathon was a slow 2:24:11 run for 33rd place – a time only two seconds quicker than the women's winner that year. He struggled to return to his previous form, but did manage to improve upon his Seoul outing the following year, taking sixth at the Rock 'n' Roll San Diego Marathon in 2:15:06. He ran two marathons in 2012: a return to San Diego saw him fare worse than the previous year, managing only ninth in 2:16:43, but his run of 2:14:53 hours for third at the Beirut Marathon was his best time and placing in a marathon since 2008.
At the 2013 Milan City Marathon he came sixth in 2:16:24, but a run of 2:13:34 at the Beirut Marathon saw him take his first victory at a race in over five years.