The inscription on the base of the trophy reads The Southern Derby: Founded A-League Season 2000 in Atlanta, Charleston, & Raleigh by those who love the Game.

At the end of the 2003 season, Charlotte moved to the USL Second Division leaving the Southern Derby to be played between only Charleston and Atlanta.

The RailHawks successfully defended their title in 2008 and through two seasons had beaten Charleston a remarkable 6 times in 6 games (4 Southern Derby fixtures).

With the Silverbacks taking a hiatus in 2009, the 2009 edition of the Southern Derby Cup was a home-and-away competition between the Charleston Battery and the Carolina RailHawks contested on May 9 and July 11.

With their return to the United Soccer League (now known as the USL Championship) in 2018, North Carolina FC (formerly the Carolina RailHawks) rejoined the competition alongside former rivals the Charleston Battery and newly minted cross-state opponents the Charlotte Independence.

Due to Covid, the Charleston Battery and North Carolina FC played a "one and done" version of the contest.

In 2021, North Carolina FC self-relegated to USL League 1 leaving Charleston and Charlotte to contest for the Cup once again.

In the case of a draw, the teams shall be declared co-champions and the Charleston Battery will retain physical control of the Cup as the 2019 champions.