Home teams listed first.
Group A
21-May	Guilford SC	2	Polonez SC	5				Pl	W	D	L	F	A	Pts
21-May	Wallingford Trout Brook	0	Yale Internationals of Cheshire	5		1	Polonez SC	3	3	0	0	17	5	9
18-Jun	Polonez SC	8	Wallingford Trout Brook	1		2	Yale Internationals of Cheshire	3	1	0	2	10	9	3
18-Jun	Guilford SC	5	Yale Internationals of Cheshire	3		3	Guilford SC	3	1	0	2	8	10	3
27-Aug	Wallingford Trout Brook	2	Guilford SC	1		4	Wallingford Trout Brook	3	1	0	2	3	14	3
27-Aug	Yale Internationals of Cheshire	2	Polonez SC	4
Group B
21-May	White Eagles	11	North Branford Over-40	0				Pl	W	D	L	F	A	Pts
20-Aug	Newington Portuguese	0	Connecticut Internationals	2		1	White Eagles	3	3	0	0	24	2	6
18-Jun	North Branford Over-40	0	Newington Portuguese	3F		2	Connecticut Internationals	3	2	0	1	18	5	6
18-Jun	Connecticut Internationals	2	White Eagles	5		3	Newington Portuguese	3	1	0	2	3	10	3
10-Sep	Newington Portuguese	0	White Eagles	8		4	North Branford Over-40	3	0	0	3	0	28	0
27-Aug	North Branford Over-40	0	Connecticut Internationals	14
Group C
21-May	Norwalk Napoli	4	Hartford Cavaliers	1				Pl	W	D	L	F	A	Pts
21-May	Newtown Salty Dogs	0	Glastonbury Celtic FC	3F		1	Glastonbury Celtic FC	3	2	1	0	8	2	7
18-Jun	Hartford Cavaliers	3	Newtown Salty Dogs	2		2	Norwalk Napoli	3	2	0	1	9	8	6
18-Jun	Glastonbury Celtic FC	4	Norwalk Napoli	1		3	Hartford Cavaliers	3	1	1	1	5	7	4
27-Aug	Newtown Salty Dogs	3	Norwalk Napoli	4		4	Newtown Salty Dogs	3	0	0	3	5	10	0
27-Aug	Hartford Cavaliers	1	Glastonbury Celtic FC	1
Group D
21-May	Greenwich Arsenal	0	Wallingford NH United	6				Pl	W	D	L	F	A	Pts
21-May	Trumbull United	2	Waterford SC	7		1	Waterford SC	3	3	0	0	19	2	9
18-Jun	Wallingford NH United	2	Trumbull United	0		2	Wallingford NH United	3	2	0	1	8	3	6
18-Jun	Waterford SC	9	Greenwich Arsenal	0		3	Greenwich Arsenal	3	1	0	2	3	16	3
27-Aug	Greenwich Arsenal	3	Trumbull United	1		4	Trumbull United	3	0	0	3	3	12	0
27-Aug	Waterford SC	3F	Wallingford NH United	0
Group E
21-May	Milford Tuesday	7	Hartford Cavaliers Over-40	0				Pl	W	D	L	F	A	Pts
21-May	Windsor United	3	New Haven Americans	0		1	Milford Tuesday	3	3	0	0	11	2	9
18-Jun	Hartford Cavaliers Over-40	0	Windsor United	6		2	Windsor United	3	2	0	1	10	2	6
18-Jun	New Haven Americans	1	Milford Tuesday	2		3	New Haven Americans	3	1	0	2	7	5	3
27-Aug	Milford Tuesday	2	Windsor United	1		4	Hartford Cavaliers Over-40	3	0	0	3	0	19	0
27-Aug	Hartford Cavaliers Over-40	0	New Haven Americans	6
Group F
21-May	Lubi Brookfield	3	North Branford	2				Pl	W	D	L	F	A	Pts
21-May	Cheshire Azzurri	7	North Haven Inter United	1		1	Cheshire Azzurri	3	3	0	0	14	2	9
18-Jun	North Branford	1	Cheshire Azzurri	4		2	North Haven Inter United	3	2	0	1	7	11	6
18-Jun	North Haven Inter United	1	Lubi Brookfield	0		3	Lubi Brookfield	3	1	0	2	3	6	3
27-Aug	Lubi Brookfield	0	Cheshire Azzurri	3		4	North Branford	3	0	0	3	7	12	0
27-Aug	North Branford	4	North Haven Inter United	5
Group Winners Who Qualify for the Quarter-Finals:
A	Polonez SC
B	White Eagles
C	Glastonbury Celtic FC
D	Waterford SC
E	Milford Tuesday
F	Cheshire Azzurri
2nd-Place Teams Who Qualify for the Quarter-Finals:
	Windsor United
	Wallingford NH United
Quarter Finals
17-Sep	Glastonbury Celtic FC	3	Polonez SC	0
17-Sep	Waterford SC	6	Cheshire Azzurri	3
17-Sep	Windsor United	2	White Eagles	1
17-Sep	Milford Tuesday	2	Wallingford NH United	5
Semi Finals (at Falcon Field, New Britain, K.O 8:15 PM)
28-Sep	Waterford SC	6	Windsor United	3
5-Oct	Wallingford NH United	2	Glastonbury Celtic FC	4
Final (at Tunxis Meade, Farmington, K.O. 7:30 PM)
19-Oct	Waterford SC	1	Glastonbury Celtic FC	1
	1-1 after full time, 1-1 after extra time. Waterford SC win 4-3 on penalty kicks.
2000 CSSA Over-30 State Cup Winners
	Waterford SC