On February 28, 2008, he won a Fair Grounds allowance race by 4½ lengths after suffering a slight injury in the Grade III Lecomte Stakes in early January.
Media darling and Derby winner Big Brown was left alone on the lead with slow early fractions in the first half mile.
However, he rebounded from that effort with a win in the Grade II New Orleans Handicap on March 14, 2009, and was named the Fair Grounds' best older horse of the year based on that accomplishment.
On June 13, 2009, he won Churchill Downs' top race for older horses in the Stephen Foster Handicap, earning his first Grade I win.
Macho Again faced a tough field of eight, including super-filly Rachel Alexandra, in the Grade I Woodward Stakes on September 5, 2009 at Saratoga Race Course at one and one eighth miles on conventional dirt.