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| Year | Date | Winner | Club | Time | Dist | Venue |
| 1890 | Sep 13 | E.E.Corner | Sydney Harriers | 24.54 | 5 mile | Botany[1st Championship] |
| 1891 | Oct 3 | E.E.Corner | Sydney Harriers | 30.09 | " | Manly |
| 1892 | Aug 6 | C.D.Morpeth | Darlinghurst Harriers | 28.09 | " | Rosehill Racecourse |
| 1893 | Aug 26 | R.C.Reid | Forest Lodge Harriers | 29.07 | " | Rosehill Racecourse |
| 1894 | Jul 14 | J.Tizard | Sydney Harriers | 29.43 | " | Kensington Racecourse |
| 1895 | Aug 31 | H.W.Biggs | Sydney Harriers | 28.29 | " | Rosehill Racecourse |
| 1896 | Aug 15 | F.J.Thomas | St. George Harriers | 30.12 | " | Kensington Racecourse |
| 1897 | Aug 28 | R.M.Gibson | Forest Lodge Harriers | 29.57 | " | Kensington Racecourse |
| 1898 | Aug 27 | S.W.York | Sydney Harriers | 29.25 | " | Kensington Racecourse |
| 1899 | Aug 26 | R.M.Gibson | Forest Lodge Harriers | 27.14 | " | Kensington Racecourse |
| 1900 | - - - | Not held due to reformation of clubs on district basis. | ||||
| 1901 | Aug 24 | S.W.York | South Sydney | 29.35 | " | Kensington Racecourse |
| 1902 | Aug 23 | S.W.York | South Sydney | 28.53 | " | Kensington Racecourse |
| 1903 | Sep 5 | S.W.York | South Sydney | 30.14 | " | Kensington Racecourse |
| 1904 | Sep 24 | H.C.Grindal | East Sydney | 29.46 | " | Kensington Racecourse |
| 1905 | Aug 26 | R.B.Fitzhardinge | Sydney Harriers | 34.35 | " | Canterbury Racecourse |
| 1906 | Aug 5 | J.O'Brien | East Brisbane H QLD | 29.50 | " | Kensington Racecourse |
| A.N.McDonald | St George Harriers | |||||
| 1907 | Sep 7 | Andrew Wood | East Sydney AAC | 35.05 | " | Terry's Estate Eastwood |
| 1908 | Chas E.Suffren Charles G.Weyman | Victoria Botany Harriers | 32.30 | " | Victoria Park Racecourse | |
| 1909 | Sep 18 | Andrew Wood | East Sydney AAC | 31.34 | " | Victoria Park Racecourse |
| 1910 | Jul 30 | Temple J.Wood | East Sydney AAC | 32.15 | " | Victoria Park Racecourse |
| 1911 | Aug 26 | Temple J.Wood | East Sydney AAC | 29.42 | " | Randwick Racecourse |
| 1912 | Temple J.Wood | East Sydney AAC | 28.54 | " | Randwick Racecourse | |
| 1913 | Sep 6 | J.Dalgleish | Botany Harriers | 28.50 | " | Randwick Racecourse |
| 1914 | Harold Hayden | Botany Harriers | 28.47 | " | Randwick Racecourse | |
| 1915 | Jul 31 | Harold Hayden | Botany Harriers | 28.14 | " | Randwick Racecourse |
| 1916 | Not held WW1 | |||||
| 1917 | Not held WW1 | |||||
| 1918 | Not held WW1 | |||||
| 1919 | Aug 23 | R.J.Fitzsimmons | South Sydney AAC | 30.10 | " | Ascot Racecourse |
| 1920 | Aug 28 | Harold Hayden | Botany Harriers | 28.11 | " | Randwick Racecourse |
| 1921 | Aug 6 | H.R.Turner | Botany Harriers | 28.35 | " | Randwick Racecourse |
| 1922 | Aug 26 | M. Jeff MacKenzie | South Sydney AAC | 27.53 | " | Randwick Racecourse |
| 1923 | Aug 18 | Frank Bailey | South Sydney AAC | 27.20 | " | Randwick Racecourse |
| 1924 | Aug 30 | Frank Bailey | South Sydney AAC | 28.22 | " | Randwick Racecourse |
| 1925 | Aug 1 | Charlie B.Weeks | St. George AAC | 27.53 | " | Randwick Racecourse |
| 1926 | Aug 28 | M. Jeff MacKenzie | Cumberland Harriers | 28.27 | " | Randwick Racecourse |
| 1927 | Jul 23 | M. Jeff MacKenzie | Western Suburbs | 34.58 | 10km | Randwick Racecourse |
| 1928 | Aug 11 | M. Jeff MacKenzie | Western Suburbs | 35.27 | " | Randwick Racecourse |
| 1929 | Aug 17 | M. Jeff MacKenzie | Western Suburbs | 34.34 | " | Randwick Racecourse |
| 1930 | Aug 16 | M. Jeff MacKenzie | Western Suburbs | 34.50 | " | Randwick Racecourse |
| 1931 | Aug 15 | Jack Sheaves | Western Suburbs | 34.57 | " | Randwick Racecourse |
| 1932 | Aug 20 | Jack Sheaves | Western Suburbs | 34.17 | " | Randwick Racecourse |
| 1933 | Jul 22 | Jack Sheaves | Western Suburbs | 33.43 | " | Randwick Racecourse |
| 1934 | Aug 4 | Jim Patterson | Botany Harriers | 35.05 | " | Randwick Racecourse |
| 1935 | Aug 3 | Jack Sheaves | Western Suburbs | 35.04 | " | Randwick Racecourse |
| 1936 | Aug 1 | Jack Sheaves | Western Suburbs | 33.15 | " | Parramatta Park |
| 1937 | Jul 31 | Ray Mettam | St. George | 35.06 | " | Randwick Racecourse |
| 1938 | Aug 13 | J.K.Stephens | Randwick-Kensington | 34.39 | " | Randwick Racecourse |
| 1939 | Jul 29 | Harry H.Hergenham | Botany Harriers | 33.44 | " | Botany |
| 1940 | Not held WW2 | |||||
| 1941 | Not held WW2 | |||||
| 1942 | Not held WW2 | |||||
| 1943 | Not held WW2 | |||||
| 1944 | Aug 5 | Harold E.Duncan | Botany Harriers | 35.58 | " | Botany |
| 1945 | Aug 4 | Donald Campbell | Randwick-Kensington | 36.27 | " | Parramatta Park |
| 1946 | Aug 3 | George Campbell | Randwick-Kensington | 33.47 | " | Centennial Park |
| 1947 | Jul 26 | George Campbell | Randwick-Kensington | 32.38 | " | Centennial Pk[50th race] |
| 1948 | Aug 7 | John Plummer | Western Suburbs | 33.53 | " | Centennial Park |
| 1949 | Jul 23 | John Plummer | Western Suburbs | 36.35 | " | Campbelltown |
| 1950 | Aug 5 | Ken Miller | Randwick-Kensington | 36.19 | " | Campbelltown |
| 1951 | Jul 28 | George Campbell | Randwick-Kensington | 36.28 | " | Campbelltown |
| 1952 | Jul 26 | Allan Lawrence | Botany | 36.23 | " | Campbelltown |
| 1953 | Jul 18 | Allan Lawrence | Botany | 38.19 | " | Carlingford |
| 1954 | Jul 31 | Graham Thomas | Western Suburbs | 38.01 | " | Carlingford |
| 1955 | Jul 30 | Allan Lawrence | Botany | 33.03 | " | Centennial Park |
| 1956 | Jun 9 | Allan Lawrence | Botany | 32.10 | " | Centennial Park |
| 1957 | Jul 27 | Dave Power | Illawarra Blue Stars | 33.14 | " | Centennial Park |
| 1958 | Jul 26 | Allan Lawrence | Botany | 33.17 | " | Centennial Park |
| 1959 | Jul 25 | Albie Thomas | St. George | 32.47 | " | Centennial Park |
| 1960 | Aug 20 | Robert 'Bob' Vagg | Eastern Suburbs | 31.50 | " | Centennial Park |
| 1961 | Aug 5 | Robert 'Bob' Vagg | Eastern Suburbs | 35.23 | " | Centennial Park |
| 1962 | Jul 29 | Robert 'Bob' Vagg | Eastern Suburbs | 34.23 | " | Centennial Park |
| 1963 | Jul 27 | Dave Power | Eastern Suburbs | 35.37 | " | Centennial Park |
| 1964 | Aug 1 | Tony Manning & | Mid-West | 35.21 | " | Centennial Park |
| Peter Manning (equal) | ||||||
| 1965 | Jul 31 | Albie Thomas | St. George | 31.51 | " | RAN Quakers Hill |
| 1966 | Aug 20 | Dave Power | Eastern Suburbs | 32.03 | " | RAN Quakers Hill |
| 1967 | May 27 | Laurie Toogood | Northern Suburbs | 29.29 | " | RAN Quakers Hill |
| 1968 | Jul 13 | Alan Harrison | Western Suburbs | 32.49 | " | Centennial Park |
| 1969 | Jun 28 | Dave Lotty | Randwick Botany | 31.25 | " | Centennial Park |
| 1970 | Jul 12 | John Farrington | Northern Suburbs | 33.33 | " | Macquarie University |
| 1971 | Jul 18 | John Farrington | Northern Suburbs | 32.08 | " | Macquarie University |
| 1972 | Jul 9 | Bruce Adams | University of NSW | 33.40 | " | Macquarie University |
| 1973 | Jun 17 | John Farrington | Ryde Hornsby | 33.05 | " | Macquarie University |
| 1974 | Jun 23 | John Farrington | Ryde Hornsby | 31.34 | " | Macquarie University |
| 1975 | Aug 24 | Rob McDonald | Sydney University | 31.43 | " | Macquarie University |
| 1976 | Aug 8 | Dennis Nee | Ryde Hornsby | 38.44 | 12km | Macquarie University |
| 1977 | Aug 24 | Dennis Nee | Ryde Hornsby | 38.28 | " | Macquarie University |
| 1978 | Aug 22 | John Andrews | Ryde Hornsby | 36.41 | " | Hawkesbury |
| 1979 | Aug 5 | Jim Murphy | Woden Valley | 38.19 | " | Macquarie Uni |
| 1980 | Aug 16 | Rob McDonald | Sydney University | 37.11 | " | Landsdowne |
| 1981 | Aug 22 | John Andrews | St George | 37.56 | " | Landsdowne |
| 1982 | May 22 | John Andrews | Ryde Hornsby | 37.07 | " | Landsdowne |
| 1983 | Jul 16 | Quentin Morley | Western Suburbs | 38.05 | " | Landsdowne |
| 1984 | Jul 18 | Steve Poulton | Western Suburbs | 39.52 | " | Landsdowne |
| 1985 | Jul 20 | Lawrie Whitty | St George | 38.22 | " | Landsdowne |
| 1986 | Aug 16 | Jamie Harrison | University of NSW | 37.54 | " | Landsdowne |
| 1987 | Aug 1 | Quentin Morley | Reebok | 37.12 | " | Landsdowne |
| 1988 | May 21 | Quentin Morley | Reebok | 38.18 | " | Landsdowne |
| 1989 | Jul 29 | Jamie Harrison | University of NSW | 37.43 | " | Landsdowne |
| 1990 | Jul28 | Glenn Ritchie | Tiger Wests | 38.30 | " | Crest |
| 1991 | Jul 14 | Clayton Clewes | Seiko Easts | 39.02 | " | Werrington |
| 1992 | Jul 25 | Paul Arthur | Seiko Easts | 34.02 | " | Crest |
| 1993 | Jul 3 | Ian Leitch | Myers Park Novo | 38.56 | " | Nowra |
| 1994 | Jul 2 | David Lightfoot | Asics Wests | 39.49 | " | Nowra |
| 1995 | Jul 29 | Paul Arthur | Athletics East | 39.37 | " | Nowra |
| 1996 | Jun 8 | Paul Arthur | Athletics East | 38.32 | " | Nowra |
The 1997 race will see the running of the 100th NSW Senior Mens Cross Country Championship.
 | In 1916 (WW1) a Metropolitan Cross Country Championship was held. |
| During WW2 non championship scratch races were held , with results as follows :Aug 3 1940 Jim Patterson Botany 35.20 10km Randwick Racecourse. Aug 10 1941 Ray Mettam Western Suburbs 35:13 10km Botany Aug 8 1942 B 'Silver' Doyle South Sydney 37:05 10km Botany Aug 7 1943 Ray Mettam Western Suburbs 36:17 10km Botany |
| In the early years a biennial Australasian Cross Country Championship was held with the first being in 1910 in Hobart. |
| The first Australian Cross Country Championship was held in 1929 in Tasmania and the 4th in 1935 at Parramatta Park. |
| BROTHERS: Three pairs of brothers have featured in the results over the years: In 1964 Tony Manning and Peter Manning dead heated for first place. Between 1907 and 1912, the Wood brothers, Andrew and Temple collected five of the six titles on offer. |
| BROTHERS: In the 1940's Don and George Campbell had close finishes. In 1947 George won from Don by a margain of 2 seconds. In 1946 the magain was 15 seconds. (But in the 10 mile cross country championship on 17/8/46, placings were reversed and Don beat George by 0.2seconds.) Other minor placings by the Campbell's were on 7/8/48 when Don was 3rd and on 5/8/50 when George was 2nd. Brisbane was the venue for the 1946 Australian cross country championships and the NSW team had two sets of brothers- Don and George Campbell and Ken and S Semple. George was the Australian Champion and the NSW team comprising the two sets of brothers (and two other runners-B Doyle and J Weeks) won the teams point score. |
| 1910 | The NSW Championship was conducted six weeks earlier then usual (July 30) to enable the State selectors sufficient time to name a team for the inaugural Australasian Cross Country Championship in Hobart on September 1st. A record entry of 235 athletes contested the event held at Victori Park Racing and Reacreation Grounds (Zetland) in ideal conditions. The NSW title was won by Temple Wood and was selected along side his brother, Andrew, for the National title. Surprisingly Andrew, the NSW captain, won the first Australasian title. |
| 1927 | The distance for the NSW Cross Country Championship was lengthened from 5 mile to 10 kilometres to keep in line with Australian, New Zealand and overseas
standards. The Australian Jockey Club once again placed the World-famous Randwick Racecouse at the disposal of the Association. |
| 1935 | To select the best NSW team the "executive decided to lay down a more severe course than in recent years"- runners had to clear 24 fences and 9 brush jumps. |
| 1939 | The 1939 event was held at Botany, was the last championships to be held before a four year break, during World War II. Virtual unknown, Botany's Harold Herbert Hergenham won a close race from Ern Evans. The following season Hergenham was one of 220 Association athletes to go to war. Corporal Hergenham, who served in the Army, was killed in action in January 1941 at Bardia. |
| 1939 | In his very first season of running, George Campbell was a very late entry into the NSW Cross Country Championship. George's brother, Donald had entered but George who had only just started running had not pre-entered. The officials eventually allowed George to run in the place of Donald. George went on to place second. |
| 1952 | The worst weather conditions recorded were in 1952 at Campbelltown when torrential rain changed a normally small creek (Fishers Ghost Creek) into a 'raging torrent' which had to be crossed four times. The Annual Report of that year states that "never before has a cross country
running championship come so close to being a cross country swimming championship." According to spectator Graham Taylor, John Plummer (the 1948 and 1949 winner) had to rescue a fellow competitor who was getting washed away down the creek. Some crossings could only occur by holding on to a safety rope as they crossed the river which was flowing at head height. The brilliant Alan Lawrence won the event. |
| 1962 | The current Australian Cross Country Champion, Robert Vagg, clinched this third straight NSW Cross Country title to add to his third win in the NSW 10 mile cross country and NSW Road Championship. During these three years (1960-1962), Robert was undoubtly the finest cross country runner in Australia. Two months later Robert won the Perth Commonwealth Games 6 mile selection trial in a brilliant 28:01.8, defeating Ron Clarke by 10 seconds. |
| 1964 | Previous winners of the event had included cross country stars Robert Vagg, Dave Power and Albie Thomas, but in 1964 two brothers from Coolah tied for the title. Peter & Tony Manning found it very difficult to train during the week as unlike the city, they had few street lights to see by during their evening training runs. Tony proved it was no fluke by winning the NSW 10 mile road championship. |
| 23 times | Randwick Race Course | '10s, '20s, '30s |
| 15 | Centennial Park | '40s, '50s, '60s |
| 12 | Lansdowne/The Crest | '80s, '90s |
| 10 | Kensington racecourse | 1890s, 1900s |
| 9 | Macquarie Uni | 70s |
| 4 | Nowra/Cambewarra | 90s |
| 4 | Campbelltown | 50s |
| 3 | H.M.A.S. Nirimba/ Quakers Hill | 60s |
| 3 | Victoria Park Racecourse | 1900s |
| 3 | Rosehill Racecourse | 1890s |
| 2 | Parramatta Park | 1936, 1945 |
| 1 | Botany 1st Army Camp | 1890 |
| 1 | Manly | 1891 |
| 1 | Eastwood | 1907 |
| 1 | Ascot Racecourse | 1919 |
| 1 | Botany | 1939/44 |
| 1 | Carlingford | 1953/54 |
| 1 | Hawksbury | 1978 |
| 1 | Werrington | 1991 |
Before the war years the N.S.W. Cross Country event was held over the distance of five miles at Racecourses around the metroplitan area the main venues being Randwick/Kensington the race was held at these venues on 37 occasions. In 1927 the event was changed to a 10 km event and although the event was still staged at Randwick other race courses were brought into use - Rosehill, Canterbury, Victoria Park and Ascot. In 1937 the race progressed to the suburbs - Manly, Eastwood and Parramatta. The event was not held in 1916 due to the reforming of the district clubs.The War years also stopped this event although non-championship events were held.
| 23 | Randwick Botany/Kensington |
| 17 | Western Suburbs/Asics Wests/Tiger Wests |
| 14 | East Sydney/East Suburbs/Athletics East/Seiko Easts/Eastern Bays-Brats |
| 9 | South Sydney |
| 7 | St George |
| 3 | Northern Suburbs |
| 3 | University of NSW |
| 2 | Sydney Harriers |
| 2 | Sydney University |
| 1 | Cumberland/Ryde Hornsby, Myer Park Novo, Illawarra |
| 6 times | M. Jeff. MacKenzie | Western Suburbs | 1922/26/27/28/29/30 |
| 5 | Jack Sheaves | Western Suburbs. | 1931/32/33/35/36 |
| Allan Lawrence | Botany | 1952/53/55/56/58 | |
| 4 | John Farrington | Ryde/Hornsby | 1970/71/73/74 |
| S.W. York | Sydney Harriers/South Sydney | 1898/1901/02/03 | |
| 3 | Paul Arthur | Athletics East/Sieko Easts | 1992/95/96 |
| Dave Power | Illawarra Blue Stars/ Easts | 1957/63/66 | |
| John Andrews | St George/Ryde Hornsby | 1978/81/82 | |
| Robert (Bob) Vagg | Eastern Suburbs | 1960/61/62 | |
| George Campbell | Randwick/Kensington | 1946/47/51 | |
| Temple J. Woods | East Sydney | 1910/11/12 |
Country-based athletes have won the state title only twice, when Dave Power in 1957 represented the Illawarra Blue Stars club, and Ian Leitch ran for Myer Park Novo in 1993, some 36 years later.
| 1910 | Andrew Wood |
| 1912 | Charles Weyman |
| 1923 | Frank Barley |
| 1935 | Jack Sheaves |
| 1946 | George Campbell |
| 1954/55/57 | Dave Power |
| 1959/61 | Robert Vagg |
| 1967 | Laurie Toogood|
| 1971 | John Farrington|
| 1982 | Laurie Whitty|
| 1994 | Wayne Larden
| Paul Arthur | 1992 |
| John Andrews | 1981, 1982, 1983 |
| Clayton Clews | 1987 |
| John Farrington | 1968, 1972, 1974 |
| James Harrison | 1987, 1988, 1989, 1990, 1991 |
| Allan Lawrence | 1954, 1956, 1960 |
| Dave Lotty | 1969 |
| Tony Manning | 1969, 1970 |
| Robert McDonald | 1975, 1979, 1983 |
| Dennis Nee | 1975 |
| John Plummer | 1950 |
| Steve Poulton | 1985, 1987, 1989 |
| Dave Power | 1956, 1960, 1962 |
| Albie Thomas | 1956, 1960, 1964, 1958, 1962 |
| Graham Thomas | 1956 |
| Laurie Toogood | 1967 |
| Robert Vagg | 1962, 1964 |
| Lawrie Whitty | 1982, 1983 |
