For five years in a row, from 2002 (at the age of 19) through 2006, he took both short (4 k m) and long (12 k m) races at the IAAF World Cross Country Championships, a feat no other runner has accomplished even once. After the IAAF eliminated the short course race in 2007, Kenenisa won a final long course race in 2008, bringing his World Cross Country medal totals to 11 senior individual gold medals (6 long course, 5 short course), 1 senior silver medal (2001), 1 junior gold medal (2001), 2 team gold medals (2004, 2005), 3 team silver medals (2002, 2003, & 2008), and 1 team bronze medal (2006) for a grand total of 19 medals.
On 17 February 2007, he broke the indoor world record over 2000 m in Birmingham, with a time of 4:49.99. His spectacular final 300 m aided this time which would be considered excellent even outdoors.
On 24 March 2007, however, his remarkable racing streak of 27 consecutive victories in cross country races (dating back to his last previous loss in December 2001) came to an end when after leading the race in the penultimate lap of the 2007 IAAF World Cross Country Championships in Mombasa he succumbed to the very hot, humid conditions (which caused more than 1/6 of all competitors to drop out) and was passed by eventual winner Zersenay Tadese on the last lap before Kenenisa dropped out. This was greeted with cheers by the Kenyan crowds, an occurrence which has been frowned upon by the wider athletics community.
On 18 November 2007, Kenenisa married Ethiopian film actress Danawit Gebregziabher in Addis Ababa. Kenenisa has one younger brother, Tariku Bekele, who is also an accomplished world-class distance runner.