Serving the Maryland Soccer Community since 1924


MSSA Cup Champions

The Rowland & Stewart Cups are Maryland's oldest cup competitions.

The H.C.W. Rowland Challenge Cup was donated by Mrs. H.C.W. Rowland in the interest of Association Football in 1914. It is Maryland's open championship. 

The Harry A. Stewart Trophy was established in 1932 as the Amateur Challenge Cup Competition. 

It is believed that in the past that these competitions qualified Maryland sides into the respective national tournaments. Since 2013, the winners have advanced to the USASA Region I qualifiers, the Rowland Cup to the Werner Fricker Cup and the Stewart Cup to the Amateur Cup.

The Morton Cup was named after Darwin "Lefty" Morton, former Vice President of the Maryland State Soccer Association. Lefty coached for many years and was also an administrator for MSSA with the Cups program & registration. Lefty could be seen every Sunday at a pitch somewhere in the state checking the local scene. The Morton Cup is a state only competition.

The Maryland Over-30 & Over-40 Cups qualify teams to represent the state at USASA Region I qualifiers.

Year Rowland Cup Stewart Cup Morton Cup Maryland
Over-30 Cup
Over-40 Cup
Over-50 Cup
2023 Christos FC Sure Sports FC Das Bierhalle FC - - -
2022 Christos FC Christos FC Das Bierhalle FC Christos FC Christos FC
2021 Columbia FC Christos FC Dream Team FC Christos FC Christos FC
2020 Christos FC Christos FC All Star United not played not played
2019 Yinz United Christos FC Colombia FC Maryland Bays Christos FC
2018 Christos FC Christos FC Starliners FC Christos FC Christos FC
2017 Christos FC Christos FC Catonsville FC
Christos FC
2016 Christos FC Christos FC Brothers United Christos FC
2015 Dulles Sportsplex
Aegean Hawks FC 
Maryland Bays Sierra Rangers ASA Charm City
2014 Maryland Bays  Maryland Bays FC Reina Christos FC
2013 Screaming Eagles  Maryland Bays FC Reina Christos FC
2012 Maryland Bays  Maryland Bays Christos FC
2011 Maryland Bays  Maryland Bays Christos FC
2010 Baltimore Bays
Baltimore Bays
2009 Christos FC  Green Turtle
2008 Baltimore Colts FC  Baltimore Colts FC
2007 Baltimore Colts FC  Baltimore Bays 89
2006 Baltimore Colts FC  Christos FC
2005 Baltimore Colts FC  Allied SC
2004 Baltimore Bays
2003 Hen's SC  Jerry D's
2002 Baltimore Colts FC  Christos FC
2001 DiPasquale FC  Christos FC
2000 Christos FC Brookland United
1999 Baltimore Colts FC  Baltimore Colts FC
1998 AC Hellas  AC Hellas
1997 Casa Mia 
Casa Mia
1996 * La Dolce Vita
1995 La Dolce Vita  Baltimore Kickers
1994 La Dolce Vita  Harford House
1993 La Dolce Vita  Hummers SC
1992 La Dolce Vita  Hummers SC
1991 La Dolce Vita  Hummers Sports
1990 Sonfast Blitz 
Hummers SC
1989 La Dolce Vita  Three Brothers SC
1988 La Dolce Vita  La Dolce Vita
1987 La Dolce Vita 
Olney SC
1986 Tommy's Lounge  La Dolce Vita
1985 Nats SC  Baltimore SC
1984 Casa Bianco SC *
1983 * *
1982 Spain SC  Apollon SC
1981 Shiflett & Horn  Hellenic SC
1980 Spain SC *
1979 * *
1978 Oakleigh United SC
1977 St. Elizabeths SC
1976 Casa Bianco
1975 Casa Bianco St.  St. Elizabeths SC
1974 Casa Bianco St.  St. Elizabeths SC
1973  *  Baltimore Kickers
1972 Italia Casa Bianco  Italia Casa Bianco
1971 Dnipro  Dnipro
1970 Bud's Tavern British Lions FC
1969 Baltimore Kickers  Baltimore Kickers
1968 British Lions FC  Leichling SC
1967 Britannica  British Lions FC
1966 British Lions FC  British Lions FC
1965 Washington
Internationals SC 
Internationals SC
1964 British Lions FC  Good Counsel SC
1963 British Lions FC  Central Valet SC
1962 Central Valet SC  Central Valet SC
1961 Sledz's Lounge  Central Valet SC
1960 St. Gerards  Maggies SC
1959 St. Gerards  Central Valet SC
1958 Central Valet SC  Baltimore Kickers
1957 Central Valet SC  Community
Jewelers SC
1956 Our Lady of
Pompei SC
Our Lady of
Pompei SC
1955 Community
Jewelers SC 
Jewelers SC
1954 Surf  *
1953 Parkville  Our Lady of
Pompei SC
1952 Our Lady of
Pompei SC 
Our Lady of
Pompei SC
1951 Our Lady of
Pompei SC 
Our Lady of
Pompei SC
1950 Our Lady of
Pompei SC 
Our Lady of
Pompei SC
1949 Ronald M. Davis SC Ronald M. Davis SC
1948 Parkville  C.K. Enterprises SC
1947 Our Lady of
Good Counsel
John Hasslinger SC
1946 John Hasslinger SC  John Hasslinger SC
1945 Combined British
No Competition
1944 Combined British
No Competition
1943 Santa Maria K.C.  No Competition
1942 Santa Maria K.C  No Competition
1941 Santa Maria K.C.  St. Casimir's SC
1940 Ruggiero  Our Lady of
Pompei SC
1939 Sixth District Little Joe's SC
1938 St. Gerards Corinthian SC
1937 Stonewall D.C. Lincoln SC
1936 Baltimore Canton No Competition
1935 Stonewall D.C. Shannon SC
1934 Bethlehem Steel Maryland Collegians
1933 Patapsco Rangers Lincoln SC
1932 Bethlehem Steel Stonewall D.C.
(first year)
1931 Baltimore Canton
1930 Baltimore Canton
1929 Baltimore Canton
1928 Patapsco Rangers
1927 Patapsco Rangers
1926 Baltimore Canton
1925 Patapsco Rangers
1924 *
1923 Baltimore
Soccer Club
1922 *
1921 *
1920 *
1919 *
1918 *
1917 *
1916 *
1915 *
1914 Sons of St. George

*Missing record

No records of Rowland Cup from 1915 to 1924
- It may be to the competition not played during WWI & not continued again until 1925.

Anyone who has any missing records or corrections, please email

Thanks to Brian Bunk of Soccer History USA for providing several winners. 




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