In the 2011 Kentucky Derby, Shackleford broke well and outran Comma To the Top for the lead passing the stands for the first time.
 He continued to lead around the clubhouse turn and into the stretch.
With about 200 yards (183 m) to go, he was overtaken by the eventual winner, Animal Kingdom, who won by 2 3/4 lengths.
 Meanwhile, Shackleford, now in second place with about 50 yards (46 m) left to go, was caught by Nehro and Mucho Macho Man.
He finished fourth by a length and a half in the field of 20.

Two weeks later, at the 2011 Preakness Stakes, Shackleford went off at odds of 13–1.
He broke from the 5 gate in a capacity field of 14.
 Passing the grandstand for the first time, Flashpoint took the lead with Shackleford at his flank in a fast 22-3/5 for the first ¹⁄₄-mile (402 m).
Down the backstretch, the leaders slowed the pace, clocking ³⁄₄-mile (1,200 m) in 1:12.01.
At the top of the home stretch, Shackleford took the  lead.
 Astrology challenged him until the 200 yards (183 m) mark.
Castanon then used the whip and Shackleford accelerated, holding off the strong late charge of Animal Kingdom to win by half a length.

Bets on Shackleford paid $27.20, $10.20 and $6.80.
With that win, Shackleford became the beneficiary of the largest payoff purse in Preakness history.
 He won $600,000 for coming in first in the Preakness and $550,000 as the XpressBet Bonus winner for a total payout of $1,150,000.

On June 11, 2011, the three year-old finished fifth in the Belmont Stakes after holding the lead for much of the race on a sloppy track.
As the pacesetter, Shackleford led throughout most of the 1-1/2 mile race, which started with a moderate quarter-mile in :23.9, then slowed to a leisurely :49.0 for the opening half, 1:14.5 for three-quarters, and 1:39.9 for a mile.
After leading the first nine furlongs, he faded in the stretch.
Winner Ruler On Ice as well as Stay Thirsty, Brilliant Speed and Nehro passed him.
In the 2011 Kentucky Derby, Shackleford broke well and outran Comma To the Top for the lead passing the stands for the first time.  He continued to lead around the clubhouse turn and into the stretch. With about 200 yards (183 m) to go, he was overtaken by the eventual winner, Animal Kingdom, who won by 2 3/4 lengths.  Meanwhile, Shackleford, now in second place with about 50 yards (46 m) left to go, was caught by Nehro and Mucho Macho Man. He finished fourth by a length and a half in the field of 20.
Two weeks later, at the 2011 Preakness Stakes, Shackleford went off at odds of 13–1. He broke from the 5 gate in a capacity field of 14.  Passing the grandstand for the first time, Flashpoint took the lead with Shackleford at his flank in a fast 22-3/5 for the first ¹⁄₄-mile (402 m). Down the backstretch, the leaders slowed the pace, clocking ³⁄₄-mile (1,200 m) in 1:12.01. At the top of the home stretch, Shackleford took the  lead.  Astrology challenged him until the 200 yards (183 m) mark. Castanon then used the whip and Shackleford accelerated, holding off the strong late charge of Animal Kingdom to win by half a length.
Bets on Shackleford paid $27.20, $10.20 and $6.80. With that win, Shackleford became the beneficiary of the largest payoff purse in Preakness history.  He won $600,000 for coming in first in the Preakness and $550,000 as the XpressBet Bonus winner for a total payout of $1,150,000.
On June 11, 2011, the three year-old finished fifth in the Belmont Stakes after holding the lead for much of the race on a sloppy track. As the pacesetter, Shackleford led throughout most of the 1-1/2 mile race, which started with a moderate quarter-mile in :23.9, then slowed to a leisurely :49.0 for the opening half, 1:14.5 for three-quarters, and 1:39.9 for a mile. After leading the first nine furlongs, he faded in the stretch. Winner Ruler On Ice as well as Stay Thirsty, Brilliant Speed and Nehro passed him.
Shackleford (horse)