Phillipp Dowling/Dooling records year 1699
I just found these records from the website of Marvin E. Berryman at http://pages.prodigy.net/berryman2/http://pages.prodigy.net/berryman2/
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Phillip Dowling/Dooling was the brother of Robert Dooling/Duling and these are the earliest records I have seen.
1699, April 26 - Phillipp Dowling, servant to Benj. Berryman was presented to the Court for judgment of his age ... divided opinions ... referred to next Court. Westmoreland Court
1699, May 31 - Phillipp Dowling, adjudged 15 years of age, ordered to serve Benj. Berryman according to law. Westmoreland Court