Impresionante joya

A los tres años, terminó segundo en dos ocasiones antes de ganar una carrera Maiden Special Weight en la reunión Oak Tree de Santa Anita el 29 de septiembre de 2006. Posteriormente, se adjudicó una carrera de hándicap el 26 de octubre de 2006, y luego finalizó el año con un segundo puesto en la pista de césped en el Sir Beaufort Stakes de Grado III de 1 milla el 26 de diciembre de 2006, en el día inaugural de la reunión de invierno 2006-07 de Santa Anita.

Awesome Gem ganó su primera carrera de stakes al comienzo de la temporada 2007, el 13 de enero, en el San Fernando Breeders' Cup Stakes (Grado II), de 1 1/16 millas , sobre pista de tierra, tras arrebatarle el liderato al favorito Midnight Lute justo antes de la meta. El castaño luego quedó en quinto lugar en el Strub Stakes ( Grado II), de 1 1/8 millas, sobre pista de tierra en Santa Anita el 3 de febrero de 2007, y terminó último en el grupo de ocho caballos del Santa Anita Handicap ( Grado I ), de 1 1/4 millas, el 3 de marzo de 2007.

Tras un breve descanso, Awesome Gem bajó de categoría y quedó segundo en una carrera de hándicap en la nueva pista sintética Cushion Track de Hollywood Park el 26 de mayo de 2007. Posteriormente, volvió al círculo de ganadores el 23 de junio de 2007, en una carrera de hándicap con opción de reclamación, también en Hollywood Park.

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. On August 19, 2007, he finished second in the 1-1/4-mile Pacific Classic Stakes at Del Mar. 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 ran as a long shot in the prestigious Grade I 1-1/4-mile Breeders' Cup Classic at Monmouth Park on October 27, 2007. On the sloppy track, he rallied and overtook 2007 Kentucky Derby winner Street Sense to earn third place. The $500,000 third-place prize effectively doubled the gelding's career earnings and made him West Point Thoroughbred's first horse to reach $1 million in earnings.

The chestnut took off the rest of the 2007 season and was sent to an undisclosed farm for rest. While he was on break, trainer Craig Dollase announced that he plans to point Awesome Gem toward the 2008 Dubai World Cup scheduled for March 29.

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.

On March 1, 2008, Awesome Gem placed seventh in the G1 Santa Anita Handicap, lacking his usual powerful drive down the stretch. On October 3, 2009, Awesome Gem won the Grade 2 Hawthorne Gold Cup Handicap at the age of 6. In July 2010, he won his first Grade I victory in the Hollywood Gold Cup against favorite Rail Trip.

In May 2011, he took the Lone Star Park Handicap in his first win that year as an eight-year-old. He got past Game On Dude for a one-length victory under Robby Albarado.

On August 22, he also won the Longacres Mile Handicap, beating Washington's favorite, Noosa Beach. On May 28, 2012, he won the Berkeley Handicap when the first over the line, Positive Response, was disqualified. Awesome Gem was favored in this race, his 50th race at the age of 9.