Charles Kamathi's marathon debut ended in disappointment as he was pushed out of a podium position in Milan.
The former world 10,000 metre champion had hoped to make an impact at the longer distance but fellow Kenyans Evans Cheruiyot and John Birgen took the took top two places in La Maratona Di Milano.
Cheruiyot, also making his debut, beat former winner Birgen by five seconds in a time of two hours nine minutes and 15 seconds. South African Norman Dlomo clocked a lifetime best of 2hr 10min 39sec in finishing third.
Yet while that trio celebrated there was no joy for Kamathi, who was hoping not only to win but also post a world-class time over what is described as Italy's quickest course.
Kamathi, who shot to fame six years ago in preventing the legendary Haile Gebrselassie from scoring a fifth successive world 10,000m success, saw his ambitions wrecked after 34 kilometres.
The former track star fell away when Dlomo powered to the front and both Birgen and Cheruiyot reacted quickly to the unexpected break.
"I was hoping to run under 2hr 7min but it wasn't to be," said Kamathi, although he remains adamant he can prove himself over the endurance distance.
While Kamathi eventually finished in 2:11.25, an intriguing three-man duel began to evolve after Dlomo took the race to the two remaining Kenyans.
However the unheralded South African, running quicker than he had ever done in the past, paid the penalty at 38km when Cheruiyot decisively hit the front.
Cheruiyot, returning to Italian soil just seven weeks after winning the world half-marathon bronze medal in Udine, looked full of running and proved it a kilometre later.
The 25-year-old, who clocked a very quick 59.05 for the half distance in Udine, utilised his speed and ended Birgen's hopes of repeating his 2003 victory.
"I'd like to thank my training partner Martin Lel for his pre-race advice," said Cheruiyot of this year's London and New York marathon winner, who paced the first 10km of the race.
Cheruiyot, who won a prize of £14,000, added: "It was a beatiful day for racing and I am happy with the time given, this was my debut."
Olympic bronze medallist Vanderlei de Lima failed in his bid to achieve the qualifier for next year's Games in Beijing.
Despite the helpful conditions, the Brazilian finished seventh and was 54 seconds short of his country's qualifying standard of 2:12.
Pamela Chepchumba was the predictable winner of the women's race, running an impressive time of 2:25.36.
The Kenyan scored a massive victory ahead of the host nation's Marcella Mancini, who finished in 2:34.59 with Hungary's Petra Teveli third in 2:35.21.
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