Former Pageant Title Holders
No Photo Available
Miss Oak Leaf Festival 2001
- Shana Elmore (Center)
Pictured with 1st Runner-Up Autumn Joncas (Left) and 2nd Runner-Up Ashley Adkins (Right)
Miss Oak Leaf Festival 1999  Ashlee Skeens Miss Oak Leaf Festival 2000 Shawna Moses
Miss Oak Leaf Festival 2002
  Jessi Sheiler
Miss Oak Hill 2003
Annette Johnson
Miss Oak Leaf Festival 2003
Kayla Childers
Miss Oak Leaf Festival 2004
Erin Thompson
Miss Oak Leaf Festival 2005
Amanda Moses
Miss Fayette County 2006
Caitlin Staunton
Miss Oak Leaf Festival 2006 Summer Wyatt
Court - Emily Shaffer, Talia Markham. Megan McCarley, & Jessica Bostic
Miss Teen Oak Leaf 2006 Jennifer Watterson
Court - Kiona Norvell
& Alex Richardson
2007 Royalty - Miss Oak Leaf Heather Crum, Miss Teen Bridge Day Alex Richardson, Miss Bridge Day Amy Comer
2007 Miss Oak Leaf Heather Crum and Miss Teen Oak Leaf Morgan Kesecker
2008 Royalty - Miss Teen Bridge Day Aimee Brinegar, Miss Oak Leaf Jessica Herndon, Miss Bridge Day Alex Richardson, Miss Teen Oak Leaf Kelsey Ward
2009 Royalty - Miss Teen Bridge Day Kalyn Bordman, Miss Bridge Day Ashton Ernst, Miss Oak Leaf Payton Whitt, Miss Teen Oak Leaf Britney Glover Shelton, Miss Fayette County Stefanie Skaggs, Miss Teen Fayette County Marissa Harler