In his 1943 book, "The History of Bell County" Henry Harvey Fuson [5](transcribed by C. Richard Mathews) offers some insight into those early years.

Mr. Grubb was assisted by Mrs. Maggie Chumley and Miss Cora Morris, who taught music and painting."

Following Westfall as principal was C. W. Gordinier from Valparaiso Normal School, who was appointed by the first city board of education.

Fuson further states: "The first class was graduated in 1894, the members being: John Miller, Jennie Dickinson, Julia Moore, Kate Colgan, Louise Park, Mary Campbell, Denta Campbell, Nell Van Gorder, Jess Rhorer, Dora Green, W. A. Purnell and Hattie Broshear."

According to an article in the August 10, 1967 edition of the Middlesboro Daily News, it was during the same time period that a separate high school was formed.

Middlesboro's second official school superintendent was Professor Samuel Littleberry Frogge who replaced Dr. Gordinier.

The high school course is the equal of that of any other city in the State of Kentucky of twice its size, being planned after the suggestions of the Committees of Ten and Fifteen.

Penmanship and music under the direction of a special teacher have been added to all the grades and the high school this year.

[10] Dr. Winfrey's time in Middlesboro ended in 1915 when he was accused of a criminal operation (illegal abortion) and breach of promise with a former teacher in the district.

The allegations filed by Miss Nannie Louise Lynn of Virginia were vehemently denied by Winfrey as blackmail, yet he was indicted.

[11] The court case, denial of the events, and his subsequent marriage to the young woman, ended Dr. Winfrey's long career in public service and the education field.

His estranged wife Anna whom he had married in 1897, indicated in a 1921 City Directory entry from Louisville, Kentucky that she was the widow of M.O.

Bernese,[15] 46, of Louisville over the heart and the bullet was lodged in the spinal column,[16] The motive was thought to have been revenge for Oaks' fourteen-year-old sister, Belma, being whipped a week prior,[17] He was sent to jail[18] Middlesboro High School was listed as a Class A accredited High School as early as 1920 under the direction of superintendent Doctor Tybee William (T.W.)

Under his leadership at Middlesboro beginning in the fall of 1921, the school system was considered the top district in the state.

As a result of Bradner's devotion and service to Middlesborough public schools, the football stadium located in downtown is named in his honor.

The large brick building housed both the high school and classrooms for downtown area elementary students.

The classically designed school was located atop a small knoll overlooking downtown Middlesboro for nearly 50 years.

Present day classes are held in the same building as MHS continues its long tradition of providing students with a quality education.

The senior class of 1996 unveiled a framed banner marking 100 years of excellence at Middlesboro High School during the graduation ceremony which is on permanent display in the Central Arts Building.

An excerpt from the article reads, "A quartette of girls sang " A Toast To Dear Old Erin" in more than an ordinary manner.

Middlesboro Loyalty is performed by the award winning marching band at football and basketball games, parades and at other times when maximum school spirit is required!

Fling out that dear ol' flag of yellow and white, Lean on thy sons and daughters, Fighting for right.

Amid the broad green fields that nourish our land, For honest labor and for learning we stand, And unto thee we pledge our hearts and hands, Dear ol' Alma Mater- Middlesboro!

Middlesboro High School students have the opportunity to participate in academic team,[23] The "Pride of the Cumberlands" Yellow Jacket Band, Beta Club, choir, DECA, drama, FBLA, FCCLA, First Priority, journalism, yearbook staff, newspaper, JROTC, Key Club, National Honor Society, Spanish club, student government, Technology Student Association, Teens Against Tobacco Use, HOSA and VICA.

In December 2012, it was announced that the "Pride of the Cumberlands" was selected outright to represent the state of Kentucky during a halftime show performance at the 2013 Outback Bowl in Tampa, Florida the following month.

Competition includes football, basketball, cheerleading, cross country, golf, soccer, fast pitch softball, tennis, track and volleyball.

Middlesboro High School won the 1998 Kentucky Class A state football championship game.

Under former coach Bill Powell, the baseball Yellow Jackets grew to become a state powerhouse and is one of the winningest programs in KHSAA history.

During football season, the street in front of the stadium is painted with the yellow jacket emblem used by the athletic programs.

On January 31, 2014, the Middlesboro Board of Education was granted a construction permit by the Federal Communications Commission (FCC) for a new Low Power FM (LPFM) radio station.