Oglesby attended Stephens County High School, where he practiced football and basketball. He had one game where he caught 3 touchdowns. He blocked 24 kicks in his high school career.
He accepted a football scholarship from the NCAA Division IIUniversity of North Alabama. As a freshman, he started all 10 games at cornerback, registering 57 tackles, 4 interceptions, 2 forced fumbles, one blocked kick and 13 kickoff returns for 335 yards (25.8 avg.).
As a sophomore, he started in 7 games, making 56 tackles and one interception.
As a junior, he collected 66 tackles (fourth on the team), 2 tackles for loss, 7 interceptions (2 returned for touchdowns), 15 passes defensed, one forced fumble and one fumble recovery. He contributed to the team having a 13–1 record, that included the first perfect 11-0 regular-season in school history, a Gulf South Conference championship and reaching the semifinals of the NCAA Division II playoffs.
As a senior, he tallied 45 tackles (one for loss), one interception, 11 passes defensed and one blocked kick. He played in the Cactus Bowl Division II All-Star Game. He finished his college career as a four-year starter, with 224 tackles (11 for loss), 13 interceptions and 38 passes defensed.
In 2015, he was inducted into the University of North Alabama Athletic Hall of Fame.[1]
On December 6, 2005, Oglesby signed with the Baltimore Ravens. He appeared in the last 3 games and had 2 special teams tackles.
In 2006, he appeared 16 games as the third cornerback, making 9 defensive tackles, 2 passes defended and 17 special teams tackles (third on the team). He was cut on September 2, 2007.[6]
Dallas Cowboys
On September 2, 2007, he was claimed off waivers by the Dallas Cowboys.[7] He appeared in 8 games, posting 2 defensive tackles and 3 special teams tackles.
On March 17, 2008, Oglesby re-signed with the Cowboys as an exclusive-rights free agent. He was cut on September 2, 2008.[8]
Baltimore Ravens (second stint)
On September 4, 2008, Oglesby was signed as a free agent by the Baltimore Ravens.[9] He had 14 tackles. Though he was non-tendered as a restricted free agent in the 2009 offseason, he was re-signed by the Ravens on March 2. He was released on September 5.[10]