I just found these two records for Phillipp Dowling/Dooling the brother of Robert Dooling/Duling.
The records came from the website of Marvin E. Berryman.
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
This makes Phillip born about 1684 and thus Robert Dooling born about 1682.
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