Miss Headland 1998-1999 – Randi Hancock won the title on the 60th anniversary of the pageant and received the Photogenic & Interview Awards as well as tied for the Essay Award. She also placed 3rd runner up in the Little Miss Headland. She is a 1998 graduate of Headland High School.

Trivia: Randi's cousin, Brooke Hancock is both a former Little Miss & Junior Miss Headland and was 1st runner up in Miss Headland. Her 2nd cousin, Allison Hancock, was Miss Headland 2002-03.

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