He represented Uganda at the 2008 Beijing Olympics, coming fourth over 5000 m. Kipsiro has won medals in the 5000 m at the African Championships in Athletics and the All-Africa Games.

At the 2006 Commonwealth Games in Melbourne, he came seventh in the 5000 m. Kipsiro placed in the top thirty of both the long and short races at the 2006 IAAF World Cross Country Championships.

He was thirteenth at the 2008 IAAF World Cross Country Championships, but came close to a medal at the 2008 Beijing Olympics that summer with a fourth-place finish in the men's 5000 m final.

[9] Kipsiro's 2010 season started with success at the 2010 IAAF World Cross Country Championships: he won the bronze medal in the men's race and led the Ugandan team to fifth place in the table.

[14] He won his fourth consecutive title at the Ugandan Cross Country Championships in February 2011, comfortably seeing off challenges from national rivals Stephen Kiprotich and Geofrey Kusuro.

[16] He missed the 2011 World Championships in Athletics as a result, but returned to defend his 5000 m title at the 2011 All-Africa Games and won for a second time running.

He was runner-up at the UAE Healthy Kidney 10K in New York, then took two prominent scalps in Wilson Kipsang and Haile Gebrselassie to win at the Manchester 10K.