Holiday took over from Edward Burne-Jones as stained glass designer at Powell's Glass Works in 1861, when Burne-Jones went to work for Morris & Co. While there, he designed over 300 windows, before leaving in 1891 to set up his own glass works in Hampstead.
St Mary & St Stephen's, in Wolsingham, County Durham, was redesigned by Sir George Gilbert Scott in 1845, with the building completed in 1848. The window for which the present drawing was a design was put in in 1866, a relatively early project for Holiday at Powell's.
In 1881 Holiday began to design stained glass for churches in America, visiting New York for the first time in 1890. In the mid-1880s he was commissioned to design a window for Christ Church, Cobble Hill, Brooklyn, and it was the present design to which he returned, albeit with some minor differences.