Soccer, the most popular sport in the world, had an early start in the old Orange Free State. According to the available evidence, the first recorded soccer or football games in Bloemfontein were played during 1876 between St. Andrews College and the Cathedral Choir. Beyond Bloemfontein, the game found an early foothold in towns like Heilbron, Kroonstad, Bethlehem, Lindley, and Jagersfontein during the 1880s and early 1890s. These developments were driven by merchants, railway workers, miners, and a range of other immigrants that made the Republic its home.
Given the absence of a coordinating body, the emerging clubs organised their own inter-town tournaments and occasional games featuring select teams such as Mines vs Town, Mother Country vs All Comers, and Home Born vs Colonial Born. As a result, four inter-town tournaments were played between 1891 – 1894. This laid an important foundation for the formal organisation of the game.
In 1894, on the occasion of the Fifth Inter-town Tournament held at Bloemfontein between the clubs Heilbron, Jagersfontein, Savages and Railways, the Orange Free State & Basutoland Football Association [an all-white body] was established. The new organisation was led by Fredrick Ringer of the Heilbron Football Club and President F.W. Reitz became its first official patron. A year later, the OFSBFA joined the South African Football Association, the national association that was established in 1892 at Kimberley.
Befitting a respectable organisation, it launched a three-layered competition namely the Borckenhagen Shield for first team clubs, the Old’s Challenge Cup for second teams, and the Reid Challenge Cup for players under the age of 18 years. The top competition was named after its donor, newspaper proprietor and editor of the De Express en Oranjevrijstatsche Advertentieblad, Carl Borckenhagen.
The Under 18 competition seemingly lasted until 1955 when it was replaced by the Nathan Woolf Cup [See attached photograph]. Launched in 1955, it lasted until 1972 [15 competitions] according to the engravings on the surface of the trophy. In addition, a new Under 16 competition, involving both junior football clubs and schools, was inaugurated in 1930. The latter, known as the Young Cup [See attached photograph] after its donor V.C. Young, was played for until 1972 – a total of 36 competitions.
Judging by the winner lists, Brebner High School was by far the most dominant force in the junior competitions of the OFSBFA for a significant period during the 20th century. They were particularly strong during the period 1955-72. Overall, they won the Young Cup a record 20 out of 36 times [1934, 1935, 1937, 1939, 1945, 1946, 1947 (shared),1949, 1950, 1955,1956, 1957, 1958, 1959 (shared), 1961, 1962, 1964, 1965, 1967, and 1972] and the Woolf Cup seven out of 15 times [1955, 1957, 1958, 1959, 1963, 1964, and 1965]. Its closest rival in the former competition was Model School who was crowned champions on five occasions [1938, 1940, 1952, 1953, and 1954], followed by Grey College [1959 (shared), 1963, 1966, and 1972], Ramblers AFC in1933 and 1947,and Christian Brothers College in 1951 and 1960. The results for the first three years of competition [1930 to 1932), as well as 1936, are, however, not listed.
The Woolf Cup similarly had only five champions during its lifetime. Other than Brebner High [1955, 1957, 1958, 1959, 1963, 1964, and1965], Grey College was the most competitive and recorded four championship wins [1960, 1966, 1967, and 1972]. Christian Brothers College won it twice [1961 and 1962] with Wanderers AFC  and Defence  with one victory each.
Bolsmann, Chris. “The 1899 Orange Free State football team tour of Europe: ‘Race’, imperial loyalty and sporting contest.” The International Journal of the History of Sport 28, no. 1 (2011): 81-97.
Botes, Marianna. 2014, Bloemfontein gedurende die bewind van president F.W. Reitz, 1889-1895: ‘n Kultuurhistoriese studie, PhD Dissertaiom (Cultural History), Free State University
Hill, Lloyd. “Football as code: the social diffusion of ‘soccer’ in South Africa.” Soccer & Society 11, no. 1-2 (2010): 12-28.
National Museum Bloemfontein Cultural Historical Collections – Trophy C.
Schoeman, Karel. 1980, Bloemfontein: Die ontstaan van ‘n stad, 1846 – 1946. Cape Town: Human & Rousseau