Given the nature of a GUID and the fact that you are using it as a Primary Key, then NO, you can not accomplish this.
If you have a secondary field that might help with the ordering then Yes, or if you had an IDENTITY field.
Based on the DateColumn specified:
Have a look at this
DECLARE @Table TABLE(
ID uniqueidentifier,
DateVal DateTime
)
INSERT INTO @Table SELECT NEWID(), '06 Jan 2009'
INSERT INTO @Table SELECT NEWID(), '05 Jan 2009'
DECLARE @GUID uniqueidentifier
SELECT @GUID = NEWID()
INSERT INTO @Table SELECT @GUID, '04 Jan 2009'
INSERT INTO @Table SELECT NEWID(), '03 Jan 2009'
INSERT INTO @Table SELECT NEWID(), '02 Jan 2009'
INSERT INTO @Table SELECT NEWID(), '01 Jan 2009'
SELECT *
FROM @Table
DELETE FROM @Table
WHERE DateVal <= (SELECT DateVal FROM @Table WHERE ID = @GUID)
SELECT *
FROM @Table