I highly recommend finding yourself a boosting partner for this. There isn't much people playing online, and most of them are pretty good at the game. Go into a Xbox Live Player Match, and choose the Ladies' 500 m Skating, as it is pretty easy and really short. If you don't have four human players, there will be some AI players against you. They shouldn't be too hard to beat.
If you don't want a boosting partner, then all I can say is good luck.
Win five events in a row and you'll get this achievement.