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Nothing for a John Callingwood or variations apprenticed 1620s so no place of origin but there are these entries which may be your John as master and the Thomas Collingwood of Walsall may be related.
Collingwood John son Thomas, Walsall, Staffs, spurrier to John Collingwood 10 Jun 1662
Collingwood Thomas son of Thomas, Walsall, Staffs to John Collingwood 20 Dec 1661
Hall Samuel to John Callingwood 25 Mar 1639
Lyne Edward to John Callingwood 8 Jan 1650/1
Makeris Robert to John Collingwood 10 Feb 1646/7
plus this one which may connect
Collingwood Edward son of John to Robert Bainbridge 1667/8
Jan