It's been a long time running - four decades to be exact - since an American woman broke the finish line tape at the New York City Marathon, but Olympic medalist Shalane Flanagan did just that on Sunday.
Keitany, who finished second with a time of 2:27:54, hugged Flanagan, who had the American flag already draped over her shoulders.
Compatriot Manuela Schar, three times a runner-up in NY, beat five-time victor Tatyana McFadden by almost three minutes to win the women's wheelchair race in 1:48.09.
Kenya's Mary Keitany, bidding for her fourth consecutive victory in the race, was 61 seconds back in second.
Kipsang, the 2014 NY champion, was three seconds back with Ethiopia's Lelisa Desisa third in 2:11:32.
In the men's race, Geoffrey Kamworwor of Kenya took first, his unofficial time clocking in at 2:10:53.
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It was Flanagan's first marathon of the year following a left hip injury in January.
More than 50,000 participants ran the world famous race and some 2.5 million people packed the streets to cheer on the athletes from around the world.
Flanagan became the first American woman in 40 years to win the title with a time of 2 hours 26 minutes and 53 seconds.
After taking the lead in the 23rd mile, the 24-year-old 2015 NY runner-up had to contend with Kipsang, whose final push brought him ever so close to his countryman. New York City is also where her marathon career began. Keitany won the last three marathons and was second to Flanagan.
Unlike last year's men's wheelchair race which came down to a photo finish and six hundredths of a second, Marcel Hug of Switzerland defended his title by a whopping 2 minutes, 19.82 seconds over John Charles Smith of Great Britain.