Before Union: Prior to transferring to Union, Cobb spent two seasons playing baseball at Northest Mississippi Community College in Boonville, Mississippi. As a freshman at Northeast, he hit .400 while committing just one error at second base, followed by a .335 effort as a sophomore. Cobb played his high school baseball at Myrtle High School under the leadership of former Union Bulldog standout Robert Gordon. While at Myrtle, Cobb helped lead his team to the 2002 Mississippi Class A State Championship in which he scored the winning run. As a junior, he posted a .412 batting average and 13 doubles. During his senior year in high school, Cobb hit .486 with 12 doubles, and two homeruns. In high school, Cobb was awarded numerous honors, including Most Improved (2001); Best Offense, Team MVP, .400 Club, Highest Average, All-Division, and All-Area Honorable Mentioned (2002); and Best Offense, Team MVP, .400 Club, Highest Average, All-Division, All-Area, and First Team All-State (2003). He also played in the the NEMCABB All-Star Game and the Crossroads Diamond League All-Star Game.