He went on to capture an allowance on October 26, 2006, and then ended the year with a second place on the turf in the Grade III 1-mile Sir Beaufort Stakes on December 26, 2006, on the opening day of Santa Anita's 2006–07 winter meet.

On July 21, 2007, Awesome Gem returned to the stakes scene to place second behind Sun Boat in the 1-1/16-mile Grade II San Diego Handicap on Del Mar's new Polytrack.

In the race, Awesome Gem made a furious closing effort down the stretch from almost last to narrowly miss overtaking the leader, Student Council, at the wire.

On September 29, Awesome Gem unsuccessfully dueled Tiago down the stretch in the 1-1/8-mile Grade I Goodwood Handicap on Santa Anita's new Cushion Track during the 2007 Oak Tree meet, losing by a nose and again placing second.

Awesome Gem made his first start of the 2008 season in the Grade 2 San Antonio Handicap at Santa Anita, placing third and besting his Pacific Classic rival, Student Council who came fifth.