The Ultimate Obstacle Challenge 2018 Photos. The 2019 challenge is setup in 3 different competitions. The first one is based on speed of completing obstacle course, the second is based on horsemanship and the third is based on Ranch Trail. The highest point winner of all 3 challenges wins the top prize for the challenge! This is also #2 in a series of 3 challenges this year. The first one is in June at the Everything Equine Extravaganza and the #3 is at Horses Got Talent in December.