[6] Kipyego settled in Mexico and in 2004, competed in the Mexican National Championship 5K in Mazatlán, where he finished third in 14:15 behind Alejandro Suarez and Rafael Sanchez.
The race featured Kenyan competition with Momanyi Evans and Philip Kemei, and several course snafus.
[9] On Aug. 27, Kipyego emerged on the world stage at the Mexico City Marathon, an IAAF Gold-labelled event.
At the halfway point, he was running in a lead pack with 2003 winner George Okworo and Mexican Alejandro Cuahtepizi.
They raced past political protesters who had been occupying the Plaza del Zócalo in support of Andrés Manuel López Obrador, garnering cheers of "Mexico!
The protest did not obstruct the race, and Kipyego pulled away from the pack to finish ten seconds ahead of Okworo for first prize and 270,000 pesos (or $22,800 USD).
On a new point-to-point course lined with an estimated 1 million spectators, Kipyego trailed Kenyans Fred Mogaka and Moses Kororia and finished third in 2:18:21.
He had been leading Teklu Deneke by several seconds, but he mistook a timing mat for the finish line and, for a brief moment, started celebrating.
When Deneke pulled up beside him, he realized the mistake and sprinted step-for-step with the Ethiopian, just edging him at the actual finish line.
[1] In 2011, he also raced the Twin Cities Marathon from Minneapolis to St. Paul, Minnesota, but dropped out with stomach issues.
There, on a cold morning in October, Kipyego found a large prize by scoring the win in a time of 2:14:53, netting him $15,000.
Chasing Daniel Tapia and Tesfaye Alemayehu through the rainy, cool weather, he sprinted to a third-place finish in 2:17:59.
[27] By 2019, Kipyego, who was now 45, was winning his age group (and masters) in races such as the Guadalajara Half Marathon, where he finished 16th overall in 1:13:11.
[28] In June 2019, he won his third consecutive masters' victory at Grandma's Marathon in 2:17:06, a few minutes behind overall winner Boniface Kongin.
With travel restrictions and then race cancelations, Kipyego would not be back to Grandma's Marathon or to defend his Detroit title.
[30] By 2021, after investing his prize money over decades, he was making enough in interest to carry him through the COVID-19 pandemic and the cancelation of most competitive races.