Go to career and choose the first event. It consists of a race, a drag race and an acrobatic event.
As long as you come in at least 2nd in the race and first in the drag races, you can do fairly poorly in the acrobatic event and still come in first.
Just do the first event 5 times in a row and the achievement will pop.
Don't drop out of the race or the streak will be broken.
I stayed in the game even after some horrendous pileups in the race.
It is almost difficult not to win this event.