He made his first senior international appearance at the 2005 World Championships in Athletics, running in the heats of the 5000 metres. 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. However, it was on the track that he made his first impact, taking the 5000 m silver medal and the 10,000 metres gold medal at the 2006 African Championships in Athletics.