The Lady In Black. The Track Too Tough To Tame. Darlington Stripes. All phrases you'd better get used to hearing a lot this weekend as the Cup schedule makes its annual trip to one of the most beloved, and classic, tracks in racing. Located in Darlington, South Carolina, and opened 69 years ago, it’s described as “A NASCAR Tradition” and it’s once-a-year race has become a great spot for the flashback weekend that this year highlights the 1990s, from the paint schemes on the cars to the fire suit fashions, and just for good measure, the track surface has taken a trip back to the ‘90s as well.

Not only do the nicknames set it apart from most other tracks, but the layout and distance and the challenges those wreak havoc on teams,...