The Dreadsox stayed in the BB/SAA Co-Rec Weekday league, Division 4 for the spring/summer 1999 season. The Dreadsox picked up a couple new players for the 1999 season. Marc “Psycho” Nagel added height at first base, and Sue “Big Boss” Foss came complete with a rowdy cheering section. (There’s nothing else quite like having a 2-year old girl in the dugout.) The Dreadsox showed great improvement, which enabled them to attain a .500 record for the first time in team history, finishing the summer season with 8 wins and 8 losses.

Upon losing a few players to work, injury, or flakiness, the Dreadsox hit the free agency market prior to the fall 1999 season. They placed a notice in the classified section of the Microsoft newsletter that they were looking for female softball players, and struck paydirt with the aqcuisitions of Susanne “Su-Xanadu” Hartsock, Susan “Smiley” Lyons, and Angela “Babble-On” Porter. They also found Barb “The Barbarian” Blakeslee as a walk-on (more acurate to say that she found them as a jog-on, as she happened to be jogging along a path next to the field the Dreads were playing on one evening, and asked if we were looking for an extra player). Unfortunately, Barb sprained her ankle a week or two later, and was injured all season.

With the help of the new players — and the continued improvement of their veteran players — the Dreadsox shattered the .500 barrier, finishing the fall 1999 season at 10-4, the best record in team history to date.