He joined Colm O'Connell's St. Patrick's school in Iten in 2000 and success followed shortly after: he was the silver medallist in the steeplechase at the 2001 African Junior Athletics Championships behind Ezekiel Kemboi.

He moved up to senior level the year after and a fourth-place finish in the short race at the 2003 IAAF World Cross Country Championships saw him help Kenya to the team title.

[1] He set a personal best of 8:10.66 minutes at the 2005 Golden Gala meeting and was third in the Kenyan trials,[2] but was dropped from the international squad in favour of the in-form Paul Kipsiele Koech.

He gained selection for the long race at the 2007 IAAF World Cross Country Championships and won his second career team title through his sixth-place finish.

[3] In 2009 he did not gain an international spot for Kenya, but had some success on the European circuit, improving his personal best to 8:08.48 minutes in a runner-up performance at the Herculis meeting[6] and taking seventh at the 2009 IAAF World Athletics Final.

[3] Kipyego ran in the steeplechase at the 2010 Doha Athletic Super Grand Prix, but this proved to be one of his last outings in the event as he switched to focus his efforts on road running competitions instead.