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Ahead of the race, Cheptegei had been out of action for over five months due to the knee injury he sustained at the World Athletics Championships, Oregon, Eugene in the summer.
Cheptegei would miss a chance to defend his 5,000m and 10,000m titles at the Commonwealth Games, Birmingham and also skipped another of elite races including the Great North Run, Newcastle, among others.
The 5,000m and 10,000m world record holder decided to concentrate on regaining full fitness wading off several opportunities to claim glory.
A fully rested Cheptegei proved that he is back to his best in Madrid posting an impressive 27:09.
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Defending champion of the course, Mohammed Katir, racing on home soil gave Cheptegei solid competition running side by side for the greater distance of the race.
However, in the closing stages, with about 3Km to go, Cheptegei surged breaking from Katir.
He won the tight race by 10 seconds beating Mo Katir and Jesús Ramos in Madrid.
In the women’s race, compatriot Prisca Chesang clocked 30:19 to win by 39 seconds from Francine Niyonsaba and Beatrice Chepkoech.