If I understood your requirements, the following is what you'll need. Offhand about your test data, everything had an id of 1 before I modified it.
Short form of what this does: Pivot the test data, check each value against the validation set, and return outliers. Only return each ID once in case of multiple failures.
declare @Table1 table
(id int,
StartDt datetime,
EndDt datetime)
insert into @Table1
select 1,'2009-11-28 00:00:00.000',''
union all
select 2,'2009-11-07 00:00:00.000','2009-11-27 00:00:00.000'
union all
select 3,'2009-07-01 00:00:00.000','2009-11-06 00:00:00.000'
union all
select 4,'2009-06-19 00:00:00.000','2009-06-30 00:00:00.000'
select * from @Table1
declare @Table2 table
(id int,
StartDt datetime,
EndDt datetime)
insert into @Table2
select 1,'2008-11-05 00:00:00.000','2009-11-06 00:00:00.000'
union all
select 2,'2007-11-29 00:00:00.000','2008-11-04 00:00:00.000'
union all
select 3,'2007-09-04 00:00:00.000','2007-09-04 00:00:00.000'
union all
select 4,'2007-07-02 00:00:00.000','2007-07-12 00:00:00.000'
union all
select 5,'2006-09-05 00:00:00.000','2007-06-21 00:00:00.000'
select * from @Table2
;WITH pivotedData AS
(SELECT id, StartDt as TestDT
FROM@Table1
UNION ALL
SELECT id, EndDt AS TestDT
FROM@Table1
)
SELECT DISTINCT
pd.ID
FROM
pivotedData AS pd
LEFT JOIN
@table2 AS t2
ONpd.TestDT >= t2.StartDt
AND pd.TestDt <= t2.EndDt
WHERE
t2.id IS NULL
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