HARD WAY: Be sure you have a high cycling skill so you don't fall of your bike easy and don't go to fast of the mountain, use your handbrake to sometimes in the corners (tapping), just stay with the first ones and don't be to fast to be in first place, it's easy to win when you stay with the first ones because they are not going that fast. EASY WAY: When doing the Chiliad challenge let the other racers finish before you. Then stop before hitting the final marker and get off. Next get out a sniper rifle and snipe all of the competitors. After each snipe you'll notice your position is going up. If you snipe them all you will be in first place, then finish.