He was from the second crop of foals sired by Lawyer Ron,[1] the American Champion Older Male Horse of 2007 when he won the Whitney Handicap and the Woodward Stakes.

In that five-furlong debut, he broke third, caught the leaders around the turn three wide and drove clear under jockey Angel Serpa to a two-length victory.

On August 25, Itsmyluckyday ran in a listed stakes race called the $75,000 Fasig-Tipton Turf Dash at five furlongs.

He broke in fourth under jockey Manoel Cruz, went three wide around the final turn, and drew clear of the field to win by three lengths.

That day, Itsmylucky broke in eighth under jockey Angel Serpa and ran in seventh down the backstretch in the mile and 70 yard contest.

[3] Three weeks later on December 15, Plesa wheeled back Itsmyluckyday in the $100,000 Dania Beach Stakes at one mile on the turf at Gulfstream Park.

He went around the final turn five wide and nearing the wire started picking off horses late, eventually finishing fourth.

The competition in the dirt race at Gulfstream Park included Breeders' Cup Juvenile Champion and early Kentucky Derby favorite Shanghai Bobby.

[4] Pacesetter Palace Malice set sizzling fractions, and all but one horse that was close to the lead fell apart in deep stretch.

Returning as a four-year-old in 2014, Itsmyluckyday had a new regular jockey in Paco Lopez and made steady improvement in his first five starts.

He then moved to Monmouth Park where he recorded wins in the Listed Majestic Light Stakes and the Grade III Salvator Mile.

In August he returned to Grade I company for the first time since the Preakness and finished second to Moreno in the Whitney Handicap at Saratoga, with Will Take Charge and Palace Malice among those behind.