The earliest reference to sport in Bowral was a cricket match between Wollongong and Mittagong that was played at Bowral in April 1871. In 1884 Oxley's paddock was used for playing cricket. In 1885 a two-day match between the English eleven and a Bowral District twenty-two was a highlight of cricket history. In the first innings England scored 132 and Bowral were all out for 14. In the second innings stumps were drawn when Bowral had lost 4 wickets for 14. On the first days play about 1000 people watched with about 1200 watching on the second day. The English cricket team visited Bowral again in 1887 and 1891. Cricket was played on Wednesdays and Saturdays. The Surveyors Camp Cricket Club was formed between 1894 and 1895 and had a name change in 1905 to Bowral Cricket Club, which continued to play.

Bowral is best known for its association with Sir Donald Bradman who arrived in the town when he was three. He played for the local school against Mittagong and scored 115 runs not out and took 8 wickets. His captain asked him to retire on 72 runs in the return match. It was then asked by the captain of Mittagong to leave Bradman out of the team or they would forfeit the match. Bradman abandoned cricket for two years after leaving school in favour of tennis. He joined Bowral Cricket Club in 1924 and had a meteoric career. In 1925 and 1926 he scored 985 runs in 9 innings. In 1927 he began playing first class cricket for St George and in 1928 he entered test cricket.

The Bowral, Moss Vale and Burradoo Turf Club were formed in 1884 with the first race meet being held on the 17th of March 1884. In 1904 The Bong Bong Picnic Race Club came into existence with the first race meet to be held on St Patrick's Day on Stennet's property. In September 1926 the Bowral Trotting Club was formed with almost 40 members.

On the 2nd of March 1889 a meeting was held at the School of Arts to discuss forming a bowling club. T Cope offered some land next to his nursery, which he was prepared to make the green and keep it in order. It was agreed to form the club with the subscription being £2/2/-. On the 30th of September 1889 the season was due to start but the club was not yet active.

On the 17th of July 1912 a meeting was held where it was decided to form the present club. It was also decided to approach the trustees of Corbett Gardens to permit a green to be put down. Permission was given and work began straight away. The clubroom was built and opened in August 1914. In 1924 a bowling green was made. On the 1st of October 1928 a clubhouse was opened which cost about £200. In March 1936 Light for Night play was turned on at Corbett Garden Green. On the 6th of October 1956 Sir John Northcott, the Administrator of the Commonwealth, opened a new brick clubhouse and two greens at Venables Park. In 1960 a third green was opened.

Bowral Lawn Tennis Club was formed on the 14th of September 1885. Land was leased in Merrigang Street with the right to purchase and 2 asphalt courts were laid down in 1896 and opened on the 22nd of August 1896. In September 1957 the Municipal tennis courts were opened in Loesby Park.

In 1889 Bowral Athletics Club was formed and a lease of land was obtained. Any profits made would go into making the ground suitable for cricket so then there would be 4 cricket grounds instead of two.

From 1884 Rugby League was played with the Bowral Rugby Club forming on the 16th of May 1891.

In 1883 a coursing track was put down at Eridge Park, which was RL Tooths property with the sport continuing for about 7 years. Lord and Lady Carrington attended a meeting there in July 1886. It was reported that coursing at Eridge Park was loosing interest and Greyhound coursing began at Loseby Park in the 1930's.

On the 4th of February 1901 the Bowral Golf Club was founded and play began on the Glebe. The club was playing on the Hon.RH Roberts property "Merilbah" in 1903. It was a nine-hole course and in 1903 a contract was let to put down nine new putting greens.

In April 1919 the Mayor opened the golf links on the Craigieburn property, which was a private course.

Bowral Council approved a site on the southern side of the municipal for a golf course in August 1935 but no actin was taken to acquire the land until 1947 when it was decided to borrow £10,000 to buy a property and establish a course. In January 1948 works began with the Hon. JJ Cahill MLA, Deputy Premier opening the course on the 15th of April 1950. On the 17th of November1948 the Bowral Country Club was established and this organisation uses this course.

On the 12th March 1927 the Bowral Trotting Club held its first horse show. The name changed in June 1927 to Bowral District Horse Show and Gymkhana and it proposed to hold an annual horse show and four to five gymkhanas. It was staged at Loseby Park. In 1936 the society began greyhound racing at Loseby Park that went for six and a half years.