1. Miss Kitty
Miss Kitty was co-manager of Jeff Jarrett and then changed her look to be the manager of Chyna. I dont think that she really deserves to be Manager of the Year more than Debra or someone else. I guess this is because of what happened at Armaggedon.
2. Debra
Jeff Jarrett was the Intercontinental champion several times in 1999, and it was mostly because of Debra. As the manager of Double J and the late Owen Hart, she was always at ringside to distract the ref while Jeff did something to win. Most famous for her puppies, mostly thanks to Jerry Lawler, she was very successful in 1999.
3. Terri Runnels
Terri was part of the Pretty Mean Sisters and was the manager of Meat, who was later known as Shawn Staziak. But after a dispute between the two, Terri went on to manage the winners of the Terri Invitational Tournament. The Hardy Boyz won her services after an amazing tag team ladder match.