-- First, let's declare the date range. I am declaring this
     -- here for the demo, but this could be done anyway you like.
     DECLARE @date_from DATETIME;
     DECLARE @date_to DATETIME;
      
     -- Set the start and date dates. In this case, we are using
     -- the month of october, 2006.
     SET @date_from = '2006-10-01';
     SET @date_to = '2006-10-30';
      
     -- insert  random dates.
     insert into randomdate SELECT
     (
     -- Remember, we want to add a random number to the
     -- start date. In SQL we can add days (as integers)
     -- to a date to increase the actually date/time
     -- object value.
     @date_from +
     (
     -- This will force our random number to be GTE 0.
     ABS(
      
     -- This will give us a HUGE random number that
     -- might be negative or positive.
     CAST(
     CAST( NewID() AS BINARY(8) )
     AS INT
     )
     )
      
     -- Our random number might be HUGE. We can't have
     -- exceed the date range that we are given.
     -- Therefore, we have to take the modulus of the
     -- date range difference. This will give us between
     -- zero and one less than the date range.
     %
      
     -- To get the number of days in the date range, we
     -- can simply substrate the start date from the
     -- end date. At this point though, we have to cast
     -- to INT as SQL will not make any automatic
     -- conversions for us.
     CAST(
     (@date_to - @date_from)
     AS INT
     )
     )
     )