John Dunlop (1823-1890) and Catherine May (Cameron) Dunlop (1816-1904)—John's father, James Dunlop (1772-1827), came to Canada from the village of Dunlop, Ayrshire, Scotland, at about age 24 (c.1796). Catherine May's father, John Roy Cameron (1786-1841), came to Canada with his parents c.1798 (at about age 12) from Scotland. Both John and Catherine May were born in Ontario, or Upper Canada, as it was called at the time of their births.
John and Catherine were the parents of Will Dunlop and Annie May (Dunlop) Macintyre, and the grandparents of Annie Marcella (Macintyre) Johnstone.
As John Dunlop died in 1890, this photo is from 1890 or earlier. I have arbitrarily assigned it a date of 1899.