According to the Plessy v. Ferguson ruling of 1896, it remained legal to separate the races in schools as long as facilities were equal. As the turn of the 20th century neared, approximately 1,788 black students attended 19 “colored” schools in Woodford County, while 2,630 students attended 28 white schools. Some African American students attended classes in private homes and a church in Big Spring Bottom due to a fire that destroyed a school in Woolridgetown. On February 11, 1899, the Versailles Board of Education awarded a contract to Porter Singleton of Lexington to replace the school with a new two-story, six-room structure, at a bid price of $3,110.00. Named for Mrs. Judy Simmons, and located on what is now Simmons Street, the school was dedicated in the autumn of 1899.

The first principal of Simmons School was Professor T.J. Smith, who was born in 1871 in Ballard County, Kentucky. He was succeeded by Professor Jesse L. Bean, from Mt. Sterling, Kentucky who served for more than 20 years. Professor Bean was succeeded in 1938 by Professor William J. Christy of Woodford County, Kentucky. As he assumed leadership, he realized that after 39 years of use, the school had become inadequate and needed to be replaced. It lacked a cafeteria, gymnasium, and restrooms, the gas stove heating had become a problem, and the roof leaked. World War II intervened though and it wasn’t until 1950, under the direction of J.W. Dennis, superintendent, that the Versailles Board of Education once again purchased land to construct a new school for African American students.

The school board appropriated $240,000 for construction of the school, and on Sept. 7, 1953, the new Simmons School opened its doors in the present location on Tyrone Pike, with Professor Christy continuing as principal. Of the eight principals who have succeeded Professor Christy, the longest serving (23 years), was Dr. Thomas P. McMillin, from Washington County, Kentucky, who served as Simmons’ principal from 1973-1996.

The 1954 Supreme Court decision of Brown v. the Topeka Board of Education brought about the beginning of the end of segregated schools. Woodford County’s new board policy, in compliance with the ruling, would force the older Simmons students to attend Versailles High School, located on Maple Street. Locally, nostalgia and class loyalties took precedence over policy, and the board was successfully petitioned to allow the senior class to finish at the new Simmons School for the 1956-57 school year. Six students however, chose to integrate that year. Integration came to all Woodford County Schools in 1961. In 1960, the Woodford County Board of Education made additions to the Simmons building, adding on six classrooms, portable walls, and the cafeteria, and Simmons became the first air-conditioned public school in Woodford County, serving 450 - 500 pupils in grades 1 - 6.

In August 1962, the current building was rededicated as Woodford County Junior High, serving grades 6 - 8. In the fall of 1964, with the opening of the new Woodford County Consolidated High School, Simmons again became an elementary school, sending its seventh and eighth graders to Woodford County Junior High in the former Versailles High School building on Maple Street. It then became Versailles Elementary No. 2 until 1967, when it was renamed Simmons Elementary School, reverting to the school's historical name. Today’s Simmons has the same mascot, the bulldog, as the original all-black Simmons School.

In 1987, another renovation was initiated and the building was rededicated under the direction of Dr. Joe Gormley, Superintendent. Fifteen classrooms and two restrooms were added to the front of the building. The library and cafeteria were expanded. Several portable walls were replaced with concrete block.

By 1995, the original building on Simmons Street had fallen on hard times. Some members of the community tried unsuccessfully to save the old school when they learned that the building was to be sold. They proposed to renovate the structure to be used as a multi-cultural center, with an African-American Museum, a reading room, a 100-125 seat auditorium, and office and general use spaces. But the necessary funding never came through and the building was razed. Townhouses now stand in its place on Simmons Street.

As the year 2000 approached, Simmons was viewed as a school of diversity whose enrollment was 83% Caucasian, 13% African American, and 4% Hispanic, Indian, Asian and other ethnic groups. In December 2000, Simmons Elementary School celebrated its centennial, placing the cornerstone from the original “Colored School” school building on Simmons Street at the Tyrone Pike site. Former students were invited to celebrate the diversity and history of the school. In celebration of its history, local artist (and Simmons parent) Anne Little was commissioned to paint a mural of the original Simmons School on the stage wall in gymnasium. A commemorative plaque was placed in the front courtyard, recounting Simmons’ long and diverse history.

Simmons added another chapter to its history at the conclusion of the 2004-2005 school year, saying goodbye to Susie Oder, principal from 1996-2005, and embarking on a major renovation of the Tyrone Pike building, under the leadership of Superintendent Paul Stahler. For the 2005-2006 school year, Simmons was housed at the former Woodford County Middle School/Versailles High School building on Maple Street. (Adding another chapter to that building's long history as well!) Simmons welcomed new principal Tammara Gilkison, who came from Garrard County High School where she was Assistant Principal.

When Simmons staff and students moved back into their renovated building at the start of the 2006-2007 school year, the most noticeable changes were made to the front entrance and office areas, adding a two-story atrium and secure entrance into the building, parent drop-off/pick-up areas, separate bus drop-off/pick-up area, and extensive landscaping. Changes inside included the reworked front office and staff work area, addition of a second computer lab, and a science classroom. Simmons also got a new roof and a geothermal heating and cooling system, a paved play area and basketball goals in back. The cornerstone from the original Simmons building was saved and placed at the front entrance, along with the 100th anniversary commemorative plaque.

At the start of the 2007 school year, Woodford County Director of Technology Jimmy Adams took over as interim principal while a search was made for a replacement for Ms. Gilkison. Larry Caudill, an assistant principal at Woodford County high school, was chosen for the job and officially began his duties at the beginning of the 2008-2009 school year.