1914
Formed in 1914 Ulster United went on to be one of the most successful clubs in Canadian soccer history. The founders included George Waring.
They were often known as the Red Handers. In 1914 they won the championship of the Third Division of the Toronto & District League and were promoted to the Second Division.
1915
Members of the Toronto & District Senior League Second Division. Earned promotion to the First Division.
Seventy per cent of their players and members volunteered for active war service in 1915.
1916
Ulster United won the 1916 Toronto & District Senior League and the Brigden Cup
1917
Won the Brigden Cup in 1917.
1918
Members of the Toronto & District Senior League.
Won the City championship and the Dunlop Shield in 1918.
1919
Members of the United District Football League.
In 1919 they won the City Championship and the Dunlop Shield.
1920
Finished in first place in the final standings of the Toronto & District Senior Soccer League.
Won the Brigden Cup by beating Willy’s-Overland by 2-1 on December 18, 1920.
1921
Members of the Toronto & District League.
1922
Members of the Inter-City League. In 1922 they won the Inter-City League.
Qualified for Eastern Finals of Connaught Cup. Defeated Montreal Grenadier Guards in the Eastern Finals.
1923
Members of the Inter-City League. Ulster United won the Inter-City League in 1923.
Qualified for Eastern Finals of Connaught Cup. Lost to Montreal C.P.R. in the Eastern Finals.
1924
President: W. Pentland
Members of the Inter-City League.
In 1924 they won
1925
President: W. Moffatt
Members of the Inter-Provincial League.
Ulster United won their first of three national championships in 1925 by beating in the Connaught Cup finals.
Won the British Consols Cup.
1926
President:
Secretary:
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Founding members of the National Soccer League.
In 1926 they won the Nathan Strauss Cup.
1927
Members of the National Soccer League.
In 1927 they strengthened their team by signing Tommy Cowan from Falkirk.
Won the Ontario Cup.
Won the British Consols Cup.
1928
Members of the National Soccer League.
Won the British Consols Cup.
1929
Members of the National Soccer League. Won the Western Section of the National Soccer League. In league games played they won 13 and tied 5.
Won the Ontario Cup in 1929.
Won the British Consols Cup.
Won the Robertson Cup.
1930
Members of the National Soccer League.
Won the British Consols Cup.
1931
Members of the National Soccer League.
Won the British Consols Cup.
1932
Members of the National Soccer League. Won the National Soccer League championship.
1933
Members of the National Soccer League. Won the National Soccer League championship.
1934
Members of the National Soccer League.
Played in 36 league and cup games. Won 28, lost 2 and drew 6. Scored 100 goals and had 30 scored against them.
Won the National Soccer League championship.
1935
Members of the National Soccer League.
1936
Members of the National Soccer League.
1937
Members of the National Soccer League.
Lost in the Dominion Cup finals to Vancouver Johnston Nationals.
Won the Ontario Cup in 1937.
Won the British Consols Cup.
1938
Members of the National Soccer League.
Won the British Consols Cup.
1939
Members of the National Soccer League.
1940
Members of the National Soccer League.
1941
Honorary President: T. R. Houston
President: George Waring
Members of the National Soccer League.
1942
President: George S. Waring
Joined the Toronto Senior Soccer League before the start of the 1942 season.
Won the Toronto City Cup. Defeated East End Canadians in the first round. In the finals they lost the first game by 6-1 to Dominion Bridge. In the second game they won 7-0. Ulster United won the round 8-1.
1943
President: George S. Waring
Members of the Toronto Senior Soccer League. The club won five trophies in the 1943 season. These were the Senior League championship, A.J. Halliwell Inter-City Trophy, J.W. Pickavant Trophy; and the 1942 Toronto City Cup and the 1943 Toronto City Cup.
In all the club played in 38 games during the 1943 season. Won 25, tied 10 and lost 3. In the Toronto Senior League they played in 18 games. Won 11 and tied 7. Total goals 62 against 25.
In the Toronto City Cup of 1943 Ulster United defeated Shipbuilders in the 2nd round 4-1 and Dominion Bridge in the third round 2-1. In the semi final they lost to M. D. No. 2 in 30 minutes overtime by 2-3. Ulster United protested the game and entered the finals. In the final they defeated King Edward 2-0. Goals for in this competition was 10 against 5.
1944
President: George S. Waring
Members of the Toronto Senior Soccer League.
1945
President: George S. Waring
Secretary: N.D. Chapman
Joined the newly-formed Ontario Major Soccer League.
Won the British Consols Cup.
1946
President: George S. Waring
Members of the Ontario Major Soccer League. During the season the Redhanders played in 50 games. Lost only three times, those being losses in exhibition matches.
Won the Dominion Cup, Ontario League championship, Consols Cup, Toronto City championship, Dunlop Cup and J. Harris Trophy.
George Waring retired as president after the season.
1947
President: Art Halliwell
Vice-president: Walter Freer
1948
Members of the Ontario Major Soccer League.
1949
Members of the Ontario Major Soccer League.
| Season | League | President |
| 1950 | National Soccer League | |
| 1951 | National Soccer League | |
| 1952 | National Soccer League | |
| 1953 | National Soccer League | Walter Freer |
| 1954 | National Soccer League | |
| 1955 | National Soccer League | |
| 1957 | National Soccer League | |
| 1957 | National Soccer League | |
| 1958 | National Soccer League | |
| 1959 | National Soccer League | |
| 1960 | National Soccer League | |
| 1961 | National Soccer League | |
| 1962 | National Soccer League |
Ulster United dropped out from the National Soccer League after the 1962 season.