Sr. Eugene Marie, S.S.N.D., nurtured Madonna Academy in its beginning years. The school's motto, "Verum, Pulchrum, Bonum" urged students to strive for truth, beauty, and goodness in their lives. In 1963, Sister Eugene Marie oversaw the first commencement exercises at Madonna Academy, which graduated 9 young women.

That same year, Br. Donald Gaskill, S.M. was appointed principal of Chaminade High School to continue to establish the Marianist traditions of education, as well as reach out to the local communities. The following year, Chaminade graduated 32 young men in its first graduating class of 1964.Madonna Academy continued to grow, and the expansion of a second wing of classrooms and the field house, or gymnasium, began in 1964. These campus buildings, along with the school's library, were completed in 1968.Br. Michael Galvin, S.M., appointed Principal of Chaminade High School in 1969, and Sr. Doris Ann Gentry, S.S.N.D., appointed Principal of Madonna Academy that same year, were primarily responsible for obtaining accreditation from the Southern Association of Colleges and Schools.

Chaminade was accredited for the first time in 1973. 

With the continued success of the two schools, further expansions began on each campus. In 1971, Sr. Doris Ann coordinated an expansion program at Madonna, which included audio/visual equipment additions to the school's library, curriculum adjustments, and air-conditioning. Fr. Richard Knuge, S.M., appointed Principal of Chaminade in 1973, began construction of the chapel and library.

Chaminade’s fifth principal, Br. Donald Winfree, S.M., supervised the construction of the Strickroth Building, named in honor of Br. John Strickroth, S.M.

Ushering in a new decade, Sr. Marie Danielle Amspacher, S.S.N.D., became Madonna's third Principal in 1980.

Fr. Chris Conlon, S.M., was appointed Principal of Chaminade in 1982. In this same year, Bro. John Campbell, S.M. was appointed the school’s first President. As President, Br. John's primary responsibility was the financial and spiritual well-being of the school.

Following in Sr. Marie Danielle's footsteps, Sr. Patricia Murphy, S.S.N.D. was appointed Principal of Madonna.

In 1986, Chaminade High School and Madonna Academy celebrated their 25th anniversaries.

Later that year, Bro. Raymond Purcell, S.M., succeeded Fr. Chris as Principal of Chaminade.

Facing declining enrollment and financial difficulties in 1988, the Archdiocese of Miami, the Superior General of the Marianists and the School Sisters of Notre Dame agreed to merge Chaminade High School and Madonna Academy.

In August of 1988, Chaminade-Madonna College Preparatory was established as a co-ed high school. Long-time Chaminade High School teacher, counselor, and administrator, Robert Minnaugh was appointed principal, and was charged with forming the new vision, combining the traditions of Chaminade High School and Madonna Academy. Fr. Dan Doyle, S.M., was named the first President of the new school. Fr. Dan was instrumental in the success of the merger.

Fr. Richard Knuge, S.M. succeeded Fr. Dan Doyle as president in 1992. In that year, Chaminade-Madonna College Preparatory was honored by the Department of Education with the Blue Ribbon School of Excellence Award.

In 1994, Br. John Campbell, S.M., was appointed President. During Br. John Campbell’s tenure as President, he worked diligently with Mr. Minnaugh to complete construction of the Einstein Building and the renovation of Marianist Hall.

Mrs. Ann McGrath was appointed interim Principal in 1997.

Mr. Patrick Snay was appointed Principal in 1998. Mr. Snay and Br. John Campbell led the school to a growth in enrollment, as well as academic and athletic success. They were instrumental in establishing the Learning Center for students with mild learning exceptionalities, as well as laying the groundwork for the construction for the multimillion dollar renovation of the athletic facilities.

Fr. John Thompson, S.M. was appointed President in 2002. Fr. John's initial responsibility was to bring to fruition the construction of the athletic fields, which were completed in 2004. Under his leadership, the school completed several other renovations, including a modernized main office building in 2006, and state-of-the-art science labs and an air-conditioned gymnasium in 2007.

Ms. Gloria Ramos was appointed principal in 2003. Through her leadership, the CMCP campus became more palpably Catholic and Marianist in its identity.

The House System was implemented in 2007. The House System complements the formal system of classroom education by organizing students into small groups to develop leadership skills and foster the Marianist commitment to community.

In 2008, Fr. Larry Doersching, S.M., joined the CMCP family as President.

The 2009-2010 school year marked Chaminade-Madonna's 50th Anniversary Jubilee. The celebration began in August 2009, with a C-M family liturgy, anniversary cake cutting ceremony, and an aerial photograph of CMCP students, faculty, and staff forming "50!" CMCP traditions and events throughout the school year continued to commemorate the rich history of Chaminade High School, Madonna Academy, and Chaminade-Madonna College Preparatory over the past 50 years. The 50th Anniversary Jubilee culminated with the 50th Jubilee Mass, celebrated by former Archbishop John C. Favalora, and Picnic on May 22, 2010.

Mrs. Teresita Vazquez Wardlow ’81 served as school principal from 2011-2015.

Mrs. Raiza Echemendia began her tenure as school principal/Assistant Head of School in 2015 and currently serves in that capacity.

Dr. Judith Mucheck was appointed President/Head of School in 2015 and currently serves in that capacity.

In 2012 the 1:1 iPad program for students was implemented.

In 2017 a standardized testing preparation program was implemented for students. In addition, an alternative daily schedule facilitated in-depth study through the utilization of alternating days per class period. Classes are 75 minutes in length. Finally, the Understanding by Design curriculum model was implemented for the purpose of more comprehensive unit planning and emphasis on problem-solving and critical thinking.