CSSA Over-30, Over-40 and Over-48/50 State Cups History (since 1992)
| Season | Age Group | Cup Name | Winner (League) | Runner-up (League) | Score Details | Comments |
|---|---|---|---|---|---|---|
| 1992 | Men's Over-30 | Kenneth T. Brown | New Haven Portuguese SC (SASL) | Celtic Old Boys FC (SASL) | 7-1 | Inaugural Men's Over-30 State Cup season |
| 1993 | Men's Over-30 | Kenneth T. Brown | New Haven Portuguese SC (SASL) | Connnecticut Internationals SC (SA | 1-1 AET [FT 1-1]after sudden-death pks | |
| 1994 | Men's Over-30 | Kenneth T. Brown | Waterbury PSC 'A' (SASL) | Glastonbury Celtic FC (SASL) | 3-1 | |
| 1995 | Men's Over-30 | Kenneth T. Brown | Cheshire Azzurri SC (SASL) | New Haven Portuguese SC (SASL) | 4-3 AET [FT 3-3] | |
| 1996 | Men's Over-30 | Kenneth T. Brown | Waterbury Morse Watchman SC (SASL) | Windsor United SC (SASL) | 3-1 | |
| 1997 | Men's Over-30 | Kenneth T. Brown | Waterford SC (SASL) | White Eagles SC (SASL) | 4-0 | |
| 1998 | Men's Over-30 | Kenneth T. Brown | White Eagles SC (SASL) | Cheshire Azzurri SC (SASL) | 3-2 | |
| 1999 | Men's Over-30 | Kenneth T. Brown | Waterford SC (SASL) | Waterbury Morse Watchman SC (S | 4-2 AET [FT 1-1] | |
| 2000 | Men's Over-30 | Kenneth T. Brown | Waterford SC (SASL) | Glastonbury Celtic FC (SASL) | 1-1 AET [FT 1-1]4-3 pks | "Kenneth T. Brown Cup" retired after third Waterford SC win |
| 2001 | Men's Over-30 | Johannes C. Heskes | Waterford SC (SASL) | Cheshire Azzurri SC (SASL) | 2-1 | |
| 2002 | Men's Over-30 | Johannes C. Heskes | Waterford SC (SASL) | Waterbury Cabo Verde SC (SASL) | 2-1 | |
| 2003 | Men's Over-30 | Johannes C. Heskes | Westport FC (SASL) | Cheshire Azzurri SC (SASL) | 2-1 | |
| 2004 | Men's Over-30 | Johannes C. Heskes | Danbury United SC (SASL) | Stratford United SC (SASL) | 5-2 | |
| 2005 | Men's Over-30 | Johannes C. Heskes | Waterford SC (SASL) | Cheshire Azzurri SC (SASL) | 5-2 | "Johannes C. Heskes Cup" retired after third Waterford SC win |
| 2006 | Men's Over-30 | Alex Lucas | Danbury United SC (SASL) | Glastonbury Celtic FC (SASL) | 3-2 | |
| 2007 | Men's Over-30 | Alex Lucas | Danbury United SC (SASL) | Waterbury Albanians SC (SASL) | 3-0 | "Alex Lucas Cup" retired after second Danbury United SC win (retired too early) |
| 2008 | Men's Over-30 | David C. Carmody | Danbury United SC (SASL) | Bristol Italians SC (SASL) | 2-1 | |
| 2009 | - | - | - | - | - | Not played during the SASL 2009 "Mini Season" |
| 2009-10 | Men's Over-30 | David C. Carmody | Club Napoli SC (SASL) | Norwalk Mariners SC (SASL) | 2-0 | |
| 2010-11 | Men's Over-30 | David C. Carmody | Club Napoli SC (SASL) | Polonez SC (SASL) | 4-1 | |
| 2011-12 | Men's Over-30 | David C. Carmody | Club Napoli SC (SASL) | Waterbury Albanians SC (SASL) | 5-0 | "David C. Carmody Cup" retired after third Club Napoli SC win |
| 2012-13 | Men's Over-30 | [Unnamed] Major | Danbury United (SASL) | Polonez SC (SASL) | 3-1 | |
| Men's Over-30 | [Unnamed] Intermediate | Greenwich la Peña (non-league) | Litchfield County Blues | Group Winnersand Runners-up | ||
| 2013-14 | Men's Over-30 | [Unnamed] Major | Danbury United (SASL) | Club Napoli SC (SASL) | 7-3 AET [FT 3-3] | |
| 2014-15 | Men's Over-30 | [Unnamed] Major | Club Napoli SC (SASL) | North Branford | 5-3 AET | |
| 2015-16 | Men's Over-30 | [Unnamed] Major | Danbury United (SASL) | Newington Portuguese (SASL) | 6-0 | |
| 2016-17 | Men's Over-30 | [Unnamed] Major | Danbury United (SASL) | Bridgeport United (SASL; now Vasco da Gama) | 3-0 | |
| 2017-18 | Men's Over-30 | [Unnamed] Major | North Branford (SASL) | Danbury (SASL) | 3-2 | |
| 2018-19 | Men's Over 30 | [Unnamed] Major | Vasco da Gama (SASL) | Danbury United (SASL) | 2-1 | |
| 2019-20 | Men's Over 30 | [Unnamed] Major | Danbury United (SASL) | Greenwich Arsenal (SASL) | 5-4 PKs (FT 1-1) | |
| 2020-21 | Men's Over 30 | - | - | - | - | No competition due to pandemic |
| Season | Age Group | Cup Name | Winner (League) | Runner-up (League) | Score Details | Comments |
|---|---|---|---|---|---|---|
| 2002 | Men's Over-40 | Bertil A. Larson | Wallingford NH United (SASL) | Hartford Cavaliers SC (SASL) | 2-0 | Inaugural Men's Over-40 State Cup season |
| 2003 | Men's Over-40 | Bertil A. Larson | Glastonbury Celtic FC (SASL) | Wallingford NH United (SASL) | 2-1 | |
| 2004 | Men's Over-40 | Bertil A. Larson | Wallingford NH United (SASL) | Glastonbury Celtic FC (SASL) | 4-1 | |
| 2005 | Men's Over-40 | Bertil A. Larson | North Branford Club Napoli SC (SASL) | Danbury United SC (SASL) | 4-0 | "Bertil A. Larson Cup" retired after third Wallingford NH United (now Club Napoli) win |
| 2006 | Men's Over-40 | Alan R. Schumann | Trumbull Tip Top SC (SASL) | New Britain Pulaski SC (CARSL) | 3-2 | |
| 2007 | Men's Over-40 | Alan R. Schumann | Southeast Rovers SC (SASL) | Cheshire Azzurri SC (SASL) | 2-0 | |
| 2008 | Men's Over-40 | Alan R. Schumann | Cheshire Azzurri SC (SASL) | Southeast Xara SC (SASL) | 3-0 | |
| 2009 | - | - | - | - | - | No competition during the SASL 2009 "Mini Season" |
| 2009-10 | Men's Over-40 | Alan R. Schumann | Glastonbury Celtic FC (SNEASL) | Greenwich Gunners SC (SASL) | 2-1 | |
| 2010-11 | Men's Over-40 | Alan R. Schumann | Rowayton FC (SASL) | Cheshire Azzurri SC (SASL) | 3-2 | |
| 2011-12 | Men's Over-40 | Alan R. Schumann | Norwalk Mariners SC (SASL) | Cheshire Azzurri SC (SASL) | 1-1 AET [FT 1-1] 4-3 pks | |
| 2012-13 | Men's Over-40 | Major Alan R. Schumann | Norwalk Mariners SC (SASL) | Wilton Ancient Warriors FC (SASL) | 2-1 | |
| Men's Over-40 | Intermediate | Orange SC (SASL) | New Haven Americans SC (SASL) | Group Winners and Runners-up | ||
| 2013-14 | Men's Over-40 | Alan R. Schumann Major | Greenwich Gunners SC (SASL) | Windsor Rovers (SNEASL) | 2-1 | |
| 2014-15 | Men's Over-40 | Norwalk Mariners | Glastonbury Celtic | 7-6 PKs [1-1 AET] | ||
| 2015-16 | Men's Over-40 | [Unnamed] Major | Glastonbury Celtic | Greenwich Pumas | 1-0 | |
| 2016-17 | Men's Over-40 | [Unnamed] Major | Waterbury Albanians (SASL) | Danbury United (SASL) | 8-4 AET | |
| 2017-18 | Men's Over-40 | [Unnamed] Major | Glastonbury Celtic | Windsor Rovers | 3-0* | *forfeit |
| 2018-19 | Men's Over-40 | [Unnamed] Major | Glastonbury Celtic (SNEASL) | Fairfield GAC (SASL | 1-0 AET | |
| 2019-20 | Men's Over-40 | [Unnamed] Major | Greenwich Gunners (SASL) | Waterbury Albanians (SASL) | 5-3 PKs (FT 2-2) | |
| 2020-21 | Men's Over-40 | - | - | - | - | No competition due to pandemic |
| Season | Age Group | Winner (League) | Runner-up (League*) | Score Details | Comments |
|---|---|---|---|---|---|
| 2010-11 | Men's Over-50 | Polonia Falcon Stars FC | Glastonbury Celtic FC (SNEASL) | 3-2 | Inaugural Men's Over-50 State Cup season |
| 2011-12 | Men's Over-50 | - | - | - | No competition this season. Not enough entrants |
| 2012-13 | Men's Over-48 | Polonia Falcon Stars FC | Greenwich Wolves | Inaugural Men's Over-48 State Cup season | |
| 2013-14 | Men's Over-48 | - | - | - | No competition this season. See 2013-14 Men's Over-40 and Men's Over-48 |
| 2014-15 | Men's Over-49 | New Britain Falcons | Guilford Black Eagles | 1-0 AET | |
| 2015-16 | Men's Over-50 | Polonia Falcon | Guilford Black Eagles | 3-2 | |
| 2016-17 | Men's Over-50 | Cheshire Azzurri | Guilford Black Eagles | 4-1 | |
| 2017-18 | Men's Over-50 | New Britain Falcons | Greenwich Pumas | 2-1 AET | |
| 2018-19 | Men's Over 50 | Greenwich Gunners | Cheshire Azzurri | 3-2 AET | |
| 2019-20 | Men's Over 50 | Cheshire Azzurri | Polonia Falcon Stars | 2-0 | |
| 2020-21 | Men's Over 50 | - | - | - | No competition due to the pandemic |
| * (All teams SASL unless indicated) |
| Season | Age Group | Cup Name | Winner (League) | Runner-up (League) | Score Details | Comments |
|---|---|---|---|---|---|---|
| 2012-13 | Men's Over-40 and Men's Over-48 | [Unnamed] Over-40 'Intermediate' / Over-48 Special State Cup | Polonia Falcon Stars FC (SASL) Winners of the Over-48 State Cup | Orange SC (SASL) Winners of the Over-40 'Indermediate' State Cup | 2-1 AET [FT 1-1] | Inaugural Men's Over-40/Over-48 Special State Cup season |
| 2013-14 | Men's Over-40 and Men's Over-48 | [Unnamed] Over-40 'Intermediate' / Over-48 Special State Cup | Glastonbury Celtic FC (SASL) Over-48 | Polonia Falcon Stars FC (SASL) Over-48 | 2-1 AET [FT 1-1] |
| Season | Age Group | Cup Name | Winner (League) | Runner-up (League) | Score Details | Comments |
|---|---|---|---|---|---|---|
| 2012-13 | Women's Over-30 | [Unnamed] | Guilden Group A Runners-up | Black Angus Group A Winners | 4-2 | Inaugural Women's Over-30 State Cup season |
| 2013-14 | Women's Over-30 | - | - | - | - | No competition this season |
