He was signed by Gretna on loan in January 2008, and made his league debut for Gretna against Rangers on 16 January 2008. He played regularly for the rest of the season at the troubled Scottish club who were placed into administration during his tenure there. Despite this Naughton continued for Gretna as the Blades agreed to cover insurance payments needed to allow him to play.. Naughton played eighteen times for the club but was unable to help them avoid relegation.
Naughton made his first team debut for the Blades the following season, coming on as a second half substitute in the first round of the League Cup against Port Vale in August 2008. In his second substitute appearance for the club he netted the winning goal in a 2-1 League Cup success over Yorkshire rivals Huddersfield Town.