[1] Bred by Gulf Coast Farms, Lookin At Lucky was bought back as a yearling for $35,000 at the 2008 Keeneland September Sale.

After working 1/8 of a mile in 10 seconds, Lookin at Lucky was bought by popular trainer Bob Baffert at the 2009 Keeneland April Sale for $475,000.

Lookin At Lucky solidified his entrance into the Breeders' Cup Juvenile by winning the Grade One Norfolk Stakes with final time of 1:43.11 in a full field of 12.

Going off as the favorite from post 13, Lookin At Lucky had a difficult trip and finished second by a head behind the long shot European winner, Vale of York in the Breeders' Cup Juvenile.

On December 19, Lookin At Lucky sealed American Champion Two-Year-Old Colt honors with a win over chief rival Noble's Promise in the CashCall Futurity.

Drawing the number one inside post, he was pinned to the rail and had nowhere to go until a late run to wind up sixth, making it his first off-the-board finish.

Lookin At Lucky went off as the 2–1 second choice and paid $6.80 to win in a time of 1:55.47, holding off pacesetter First Dude and the late-charging Jackson Bend.

Entering the far turn while still 3 paths wide, he moved past his competitors, winning the race by four lengths over upcoming Trappe Shot, followed by First Dude and Super Saver, the Kentucky Derby winner.

Still in eighth place on the backstretch, Lookin At Lucky came five-wide around the far turn, caught the leader in late home-stretch and won by 11⁄4 lengths.