2011

Quarterfinals @Higher Seeds

#1 Sacred Heart Academy 3, #8 North Haven 0

#5 Cheshire 1, #4 Guilford 0

#2 Shelton 4, #7 Mercy 2

#3 Amity 3, #6 West Haven 1

Semifinals @Higher Seeds

Cheshire 1, Sacred Heart Academy 1 (Cheshire advances via penalty kicks, 3-0)

Shelton 1, Amity 0

Championship @East Haven HS

Cheshire 1, Shelton 0

2010

Quarterfinals @Higher Seeds

#1 Hamden 2, #8 North Haven 1

#2 Shelton 7, #7 Branford 0

#3 Cheshire 3, #6 Guilford 0

#5 Amity 1, #4 Hand 0

Semifinals @Higher Seeds

Hamden 3, Amity 0

Shelton 1, Cheshire 0

Championship @East Haven HS

Shelton 1, Hamden 0

2009

Semifinals @Higher Seeds

#1 Hand 1, #4 Mercy 1 (Hand wins via penalty kicks, 3-2)

#3 Cheshire 2, #2 Wilbur Cross 1

Championship @East Haven HS

#1 Hand 0, #3 Cheshire 0 - co-champions declared

2008

Semifinals @Hamden HS

#4 Hand 1, #1 Cheshire 0.

#2 Wilbur Cross 2, #3 Mercy 0

Championship @Shelton HS

Hand 2, Wilbur Cross 0

2007

Semifinals @Foran HS

#4 Mercy 1, #1 Hand 0

#2 Cheshire 2, #3 Branford 1

Championship @East Haven HS

Cheshire 2, Mercy 0

2006

Semifinals@Foran HS

#1 Amity defeated #4 North Haven, 5-1

#3 Mercy defeated #2 Hand, 2-1

Championship@East Haven HS

Amity 1, Mercy 0

2005

Semifinals@Foran HS

#1 Cheshire 5, #4 North Haven 0

#3 Mercy 2, #2 Hand 2 (Mercy wins 4-2 penalty kicks)

Championship @Shelton HS

Cheshire 6, Mercy 1

2004
Semifinals@Foran HS
#1 Hand 3, #4 North Haven 0
#3 Cheshire 2, #2 Mercy 1
Championship@Shelton HS
Cheshire 2, Hand 1

2003
Semifinals (Strong Stadium, West Haven)
#2 Cheshire 2, #3 Hand 0
#4 Mercy 1, #1 Guilford (5-4, PK)
Championship (Guilford HS)
#4 Mercy 0, #2 Cheshire 0 - co-champions declared

2002
Semifinals (Sachem Field, North Haven)
#1 Guilford 5, #4 West Haven 0
#2 Amity 2, #3 Hand 1
Championship (Sachem Field, North Haven)
Guilford 4, Amity 2

2001
Semifinals (Sachem Field, North Haven)
#1 Guilford 4, #4 North Haven 2
#3 Amity 4, #2 Mercy 1
Championship (Sachem Field, North Haven)
Guilford 5, Amity 0

2000
Semifinals (Sachem Field, North Haven)
#2 Mercy 2, #3 Lyman Hall 1
#1 Guilford 2, #4 Shelton 1 (OT)
Championship (Sachem Field, North Haven)
Guilford 2, Mercy 1 (OT)

1999
Semifinals (Sachem Field, North Haven)
#3 Guilford 2, #2 Shelton 1
#1 Hand 1, #4 Mercy 0
Championship (Sachem Field, North Haven)
Hand 1, Guilford 0 (OT)

1998
Semifinals (Lyman Hall HS, Wallingford)
#2 Hand 3, #3 Sheehan 0
#4 Lyman Hall 3, #1 West Haven 0
Championship (Strong Field, Madison)
Hand 3, Lyman Hall 0

1994-97
No postseason tournament