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Rodger Wright was the Trinity College School's tenth Headmaster. Wright attended Upper Canada College (class of 1970) and graduated from the University of Toronto in 1974. He taught Physical Education at Upper Canada College for nine years and served as Department Head and Seaton's Housemaster. In 1983 Wright became Headmaster of Trinity College School and held this position until 2004. During his tenure as Headmaster, the Junior School was revitalized, I.T. was introduced, Le Van Hall was built, student enrollment doubled, and co-education was implemented. Wright left Trinity College School to become the Head of Collingwood School in Vancouver for 12 years, until his retirement in 2016.

In 1915 a Junior School at Trinity College School was established for boys under 15, with 16 students. Although they had a separate classroom, dormitories and table at meals, they were housed in the main school building along with the older boys.

A new Junior School building with facilities for 78 boys aged seven to 14 was opened in 1924. It was built as a memorial to those Old Boys who gave their lives during WWI. Howard Boulden was named the master in charge of the Junior School (today known as Boulden House).

Mr. Charles Tottenham was appointed head of the Junior School in 1941, a post he held for the next 40 years. Due to the declining enrolment of younger students, the Junior School was closed in 1981 and Charles Tottenham retired.

The Junior School re-opened in Boulden House in 1999 under the direction of Barbara Piccini. Barbara Piccini served as Head of the Juinor School until retiring in 2018. Jennifer Wyatt succeeds Ms. Piccini as Head of the Junior School.

Founded circa 1895, the Old Boys' Association was an organization of Trinity College School alumni. Today, the organization is known as the Trinity College School Alumni Association.

The Board of Governors is one of the main governing bodies of Trinity College School. The contemporary role of the board of governors is to act as a steward of the mission of the Corporation of Trinity College School and to be responsible for overseeing the School’s strategic direction in this regard. The board of governors is the primary policy-making body for the School.

Trinity College School was founded in Weston, Ontario. It officially opened in the home of William A. Johnson, the School's founder, on May 1, 1865. There were nine students and faculty. The school grew, and in three years' time larger quarters were needed.
The leading citizens of Port Hope, anxious to have the School located in their town, offered to pay three years' rent on premises suitable for a school. The offer was accepted and Trinity College School opened in Port Hope in September 1868.
During the next thirty years, under the direction of Headmaster Charles Bethune, Trinity College School grew from the motley collection of wooden sheds and buildings which existed initially at the site in Port Hope into a prosperous, thriving academic community.
On a wintry night in 1895 an explosion of a coal oil lamp in one of the master's rooms started a fire which destroyed almost the entire School. No one was hurt and the School was rebuilt in only eight months.
A second disastrous fire occurred in 1928. Again, virtually all of the School was destroyed. But rebuilding the School was not an easy task this time. Although TCS had received promises of funds to help with the reconstruction from the Old Boy community, on the heels of the fire came the Great Depression and many Old Boys had to withdraw their promises.
In 1933, Trinity College School's newly appointed headmaster, Philip Ketchum, found himself in charge of an institution on the brink of bankruptcy. He spent the first few years of his tenure trying to raise funds to pay off a very onerous mortgage. But, through the generosity of a handful of Old Boys, the debt was finally retired.
Throughout the mid-century period, the School experienced tremendous growth in both admissions and facilities under the leadership of Headmaster Ketchum and Junior School principal Charles Tottenham.
Due to the declining enrollment of younger students, the Junior School was closed in 1981 and Charles Tottenham retired. In 1991 The School became co-educational, enrolling its first female students. The Junior School would re-open in 1999 under the leadership of Junior School Head Barbara Piccini.
Today, Trinity College School prepares both boarding and day students for post-secondary education at universities around the world.

Charles Tottenham was born in 1914 in England and moved to Canada in the 1930s to attend Queen's University. In 1941 Tottenham was hired as the Head of the Junior School, or Boulden House, as it was known at the time. He taught History, Geography, and English at the Junior School. Tottenham retired in 1981 and continued to live at Boulden House until his death in 2006 at the age of 92.

Gordon Anderson Thetford (1895-1969) attended Trinity College School from 1911-1915. He was a prominent athlete winning the Grand Challenge Trophy in 1915, as well as several other medals for track and field.

The TCS Parents' Guild was founded as The Ladies' Guild in 1902. Comprised of mothers of TCS students, the organization's original mandate was “to complete the chapel and other interests of the School.” Today, the TCS Parents' Guild "enriches the lives of TCS students by providing special touches which enhance their physical, social and general well-being." Since 1993 the Guild has organized the annual Bear Fair.

Trevor Spottiswoode Tait was born March 20, 1897 to father William Lesesne Tait, Esq. and Florence Amelia Tait of Norfolk, Virginia. Trevor had two siblings: Arthur Lesesne Tait and Dorothy Lancaster Gray. Trevor attended Trinity College School from 1907-1913. Arthur attended also attended TCS from 1907-1912. Trevor married Katharine Stymetz Lamb Tait, a stained glass artist. He died March 10, 1984.

The Honourable James 'Jim' Bonham Strange Southey was born in 1926 in Bowmanville, Ontario. He attended Trinity College School from 1941-1944. Following TCS he attended Queen's University and Osgoode Hall, where he was a silver medalist in 1953. Jim was appointed to the Supreme Court of Canada in 1975. He served as president of the Canadian Judges' Conference, the Ontario Superior Court Judges' Association, and the Lawyers' Club of Ontario. He was also Chair of the Board at Trinity College School and was an early advocate of Co-education at the School. Jim died on July 29, 2016 in his 90th year.

Oswald George Shepherd attended TCS from 1907-1910. His father was E.H. Shepherd, Esq. from North Bay, Ontario. He played First Football and Hockey while he attended the School. He served in both WW1 (Lieutenant with the 159th Battalion Canadian Infantry) and WW2 (Lieutenant-Colonel and District Dental Officer in the C.D.C. at M.D. 7).

Norman Seagram was born July 10, 1936 in Toronto to father Norman O. Seagram, a lawyer. Norman Seagram, Jr. entered Trinity College School in 1947 and graduated in 1952.

Charles J. Seagram was born May 20, 1918 in Orillia to father J.H. Seagram. Charles Seagram entered Trinity College School in 1929 and graduated in 1936.

Ken Scott was born in 1924. He attended Trinity College School from 1940-1943, and serves as year chair for his class, and honorary trustee of the School. Ken is a veteran of WWII who served in the Royal Canadian Navy for 22 years. He came to Canada from his native England as one of the young men invited here to escape the war in Europe. Upon his graduation from TCS, he headed overseas to join the Allied effort, serving as a Officer on the HMS Ironbound and HMCS Crescent and was later promoted to Lieutenant. After the war, Ken returned to Canada and had a successful career at the Dominion Life Assurance Company.

Angus Cheever Scott was born in 1925 to parents Silas Warren Cheever Scott and Marie Louise (nee Morris). He attended Hillfield School and Ridley College. In 1943 Scott entered Trinity College at the University of Toronto. Scott left the university in 1944 for active service with the Royal Navy Volunteer Reserve. Returning to U of T, Scott graduated with a BA in Modern History in 1949. He taught for a year at Appleby College before leaving for Emmanuel College at Cambridge University, where he earned an MA in 1952. In September 1952, Scott joined the staff of Trinity College School in Port Hope as a History teacher. He became Brent Housemaster in 1955 and Assistant Headmaster in 1959. After one year’s leave of absence to attend Harvard, Scott became Trinity College School’s Headmaster in 1962. He held this position until his retirement in 1983. During his tenure as Headmaster teaching standards improved, the School endowment grew, the athletic programs were expanded, and the student advisor program was introduced. Scott died on July 5, 2001.

Tony Prower is an alumnus of Trinity College School, class of 1946. He was a music master at Trinity College School from 1951-1991. While at TCS, Prower was head of the Glee Club, the Music Club, music director of the Dramatics Club, and coached Middleside Football. Presently, Prower serves as an Honorary Trustee at TCS.

Edwin Nash (1895-1989) grew up in Froyle, Hampshire, England, where as a young boy he began gardening for the Vicar at the local Anglican church. It was at this time he was also trained in motor mechanics. In 1919, while still in England, Mr. Nash was hired by Trinity College School. He arrived in September of that year and while only intending to stay in Canada for two years, remained an employee of the school for more than 65 years. He served as Building Maintenance Supervisor and Chief Groundsman. Working under four Headmasters (Orchard, Ketchum, Scott and Wright), Nash was credited with saving the school from the devastating fire of 1928. Following the fire, Mr. Nash continued to serve T.C.S. at its temporary location in Woodstock, Ontario. There, he traveled once a week to town with laundry through all kinds of weather. While at T.C.S. Mr. Nash painted buildings, mowed and rolled lawns, maintained the gardens, and cleared snow from the roads and rinks. His favourite memories of T.C.S. included operating the School's Fordson tractor purchased in 1933 for $75 and the time one of the School's goats ate the tulips he planted for Speech Day. He was also well known for repairing the school's cricket bats. The Edwin Nash Garden at T.C.S. was dedicated to Mr. Nash in 1985.

Peter Levedag was born in 1939 and attended Trinity College School from 1951-1958. While at TCS, he was a Bethune House officer and played on the football and swim teams.

John Exton Lennard (1903-1989) attended Trinity College School from 1919-1922. He received a Distinction Cap for his performance as the best outside wing in the Little Big Four Football League. His brother, Samuel Bertram Lennard (1905-1981), attended the school from 1919-1923 and won the Challenge Cup for the best all-around school cadet and was a Triple Colour award winner making the school's first football, hockey and cricket teams. He later went on to attend the Philadelphia Textile School. Both brothers worked at S. Lennard and Sons Ltd (The Lennard's Mill) upon graduation.

Tom Lawson is an alumnus of Trinity College School, class of 1947. He worked at TCS from 1955 to 1988 as an English teacher. During that time he served as the Ketchum Housemaster and from 1978 to 1988 as the Head of the English Department. He was also founder of the Social Services Corps, and a great advocate of student debates. He received his B.A. from the University of Toronto, his M.A. from King's College, Cambridge and his Ontario Teacher's Certificate. Presently, Lawson is an honorary trustee at TCS.