During this period the school moved twice, first to a property on Darlaston Road and then to a building adjoining the All England Lawn Tennis Courts.

[1] Finally, in 1893. the college acquired the former site of Wimbledon School on Edge Hill, aided by the financial backing of Edith Arendrup.

[2] In September 1898, the Wimbledon College Army Department was established, which trained young men for entrance into the Royal Military Academies at Sandhurst and Woolwich.

[1] During the First World War, the college lost 129 former pupils, including Maurice Dease and Gerald Robert O'Sullivan, both of whom received the Victoria Cross.

[2] In 1929, eight acres of field beside Coombe Lane, in Raynes Park, was bought as a venue for the college's sporting activities; it has been in use for these purposes ever since.

[3] In 1933, due to the growing number of pupils, the decision was made to buy Donhead Lodge, across the road from the college on Edge Hill, and establish a preparatory school there.

Acting on concerns of fire hazards due to crowded corridors and underfunded laboratories in a 1938 inspection, and on the appetite from inspectors for his plans to expand the provision of geography lessons, Sinnott made plans to expand the college with new facilities; however, he was frustrated by the outbreak of the World War II, when tight restrictions were placed on the use of steel and timber.

[3] On the night of 18 February 1944, a bomb exploded on the Convent of the Sisters of Mary, situated on the Downs, a nearby road, killing five nuns and wounding several others.

[2] The college lost fifty-eight former pupils as a result of the Second World War, including Eugene Esmonde, a recipient of the Victoria Cross.

[3] Separately, during this time, Sinnott had concluded that the independent school model was not suitable, owing to the unaffordable fees required of Catholic families; in January 1942, he applied to Surrey County Council (in whose jurisdiction Wimbledon resided at the time) for deficiency aided school status,[3] and this was granted in 1943.

In order to accommodate all students, it began to use the parish halls of the next-door Sacred Heart Church, for lessons and study spaces, and facilities in Chessington owned by the Old Wimbledonians Association.

[2] In 1968, the school successfully revived its houses tradition, which had fallen into irrelevance to many boys, and prefects resumed their function as the main guarantors of discipline.

Notable players from this time were numerous and many went on to represent Surrey Schools as well as England Schools and a number went on to play first class rugby both in England and abroad (notably Brian Mullin of London Irish and Clermont, John Travers Rosslyn Park, Fergus Timmons Rosslyn Park and Cambridge, James Dyson Richmond, Brian Gegg Harlequins and Cambridge and Ben Ryan Cambridge, West Hartlepool, coach of England sevens 2007-13, Fiji sevens 2013-16 winning Olympic gold in 2016.

Discipline has been considerably emphasised since 2011, with increased security measures, electronic staff passes and registers,[2] and policies targeted at improving attendance, punctuality, homework completion rates and the orderliness of pupils.

In the provision of teaching, the college has been organised by departments since the 1980s, with shared departmental staff rooms and subject-specific blocs and classrooms.

In accordance with traditions in English Jesuit schools, Wimbledon College students are organised into a system of 'lines' rather than year groups.

The school organises annual interhouse competitions, including in music, debating, spelling bees, subject quizzes, rugby, football, cricket and dodgeball.

For participation in these interhouse competitions and for good behaviour and positive contributions in school, students in the Lower and Higher Lines are awarded with house points which accumulate over the course of a year.

The Sixth Form remains to be fully amalgamated into the house points system, with many of the interhouse competitions weakly attended by those in Poetry and Rhetoric.

Over the history of the college, prefects at times had a considerable and sometimes essential role in the day-to-day organisation and discipline management of the college;[2] however, they now enjoy considerably less authority and prefects are now mostly called upon to represent the school at public events, such as at open days, and assisting teachers when required logistically, such as when escorting pupils to venues in public.

[16] In order to recognise the achievement of its pupils in certain fields, such as music, sports and extracurricular activities, the college annually awards high-performing students honorary ties, known as 'colours'.

Students at the Ursuline High School additionally have extensive non-reciprocal access to study resources at Wimbledon College, including its sixth form centre.

[2] In the academic year 2016–17, opportunities offered specifically to boys at the sixth form included eucharistic ministry at the school's Masses, an annual homeless sleep-out in the grounds of the college in support of local homelessness charities, pilgrimages, topical panels, peer mentoring and subject-specific clubs.

[14] Until recently, under the 'Project Manvi' scheme, Wimbledon College would invite sixth form pupils to visit a school in India with which it was partnered and had helped to establish.

Simon Potter MBE started the collaboration with the Ursuline, and produced, directed, adapted or wrote 67 plays and musicals between 1972 and 2022.

The Strings Project, established in 2005, gives 50 boys in Figures the opportunity to learn the violin, viola, cello, or the double bass.

[31][14] The college is home to 136 Detachment, part of South West London Army Cadet Force, which wears the cap-badge of the Princess of Wales's Royal Regiment.

The ACF offers young people the opportunity to take part in activities such as field-craft, navigation, skill-at-arms, first aid, shooting, drill, sports, and the Duke of Edinburgh's Award (Bronze, Silver, and Gold).

[16] The school also has a strong focus on characters and virtues in the wider context of spiritual development, a fundamental aim of Jesuit education.

[35][36] Additionally, the Old Wimbledonians Association organises the Sinnott Society, a biannual group which meets to hear talks from other alumni alongside current Sixth Form pupils.