Gilmore attended South Pointe High School in Rock Hill, South Carolina, where he played football, basketball and ran track. In football, he was a two-way player as quarterback and defensive back, and helped his team to a perfect 15–0 record and the SCHSL AAAA Division II title as a senior. Among his teammates were DeVonte Holloman and Jadeveon Clowney. Playing quarterback on offense, Gilmore rushed for 1,331 yards and 23 touchdowns and passed for 1,771 yards with 14 scores. He earned first-team all-state honors by The State and was named an All-American by Parade and EA Sports. He was also named Mr. Football for the state of South Carolina.
In track & field, Gilmore competed as a sprinter during his junior year in 2008. He recorded a PR of 11.41 seconds in the 100 meters in the prelims of the Taco Bell Classic. At the York County Meet, he took 5th in the 200 meters, at 23.14 seconds, and placed 9th in the 400 meters, with a time of 54.94 seconds. He was also a member of the 4 × 100 m relay (43.10s) squad.
Considered a four-star recruit by Rivals.com, Gilmore was listed as the No. 2 overall prospect from South Carolina in the class of 2009. He chose South Carolina over Alabama, Tennessee, and Clemson.

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