[3] She started training with Sing'ore Girls, under running coach Boniface Tiren, and worked alongside other promising young runners, including future world champions Janeth Jepkosgei and Vivian Cheruiyot.

The 21-year-old Cherop had begun training with a prominent group of road athletes, including Chicago Marathon winner Evans Rutto and Boston champion Lameck Aguta.

She led alongside Svetlana Ponomarenko for most of the race but she was overhauled by the Russian and Alena Vinitskaya in the final mile, having to settle for third place with a time of 2:38:45.

[14] She took on the classic distance for a second time in April 2008 at the Country Music Marathon in Nashville, where Ponomarenko again took top honours while Cherop (15 years her junior) finished in fourth place.

[17] In the women's 15 km race at the Baringo Half Marathon in December 2009 she engaged in a race-long battle for the lead against Agnes Kiprop, although she faded in the final stages and was runner-up in 52:01 minutes.

[18] The following year she entered the Hamburg Marathon and ran a solo effort to win the race and a significant personal best of 2:28:38 – over five minutes quicker than her previous time.

[19] This mark did not stand for long as she improved again at the Toronto Waterfront Marathon in September 2010, where she fell over mid-race but recovered to hold off Tirfi Tsegaye to win the race in a time of 2:22:42 – the fastest ever run in Canada, beating Romania's Lidia Șimon's all-comers record set at the 2001 World Championships in Edmonton.

[25] Three months later she ran at the 2012 Boston Marathon and defeated Jemima Sumgong in a sprint finish to win the race a time of 2:31:50 hours (slowed by warm temperatures).