Along with several other prominent members of the "McChord" (now First) Presbyterian Church, including John C. Breckinridge, the group drew up the school's articles of incorporation.

In 1947 the high school grades were discontinued, and the boarding rooms were leased to the University of Kentucky.

In March–April 2017, Sayre begun the demolition and reconstruction of the lower (elementary) school, only finishing in summer of 2018.

[5] Notable past Sayre students include Nobel Laureate William Lipscomb,[12] woman suffragist Laura Clay, settlement school founder Katherine Pettit, Josh Hopkins,[13] Byrd Spilman Dewey and actress Ashley Judd.

[3] Former NFL and Marshall University quarterback Chad Pennington was hired in 2018 to be coach of Sayre's new football team.