[2] In November 1892 he sat and passed the entrance examinations for the Royal Military Academy at Woolwich, but in that year there were more successful applicants than places available, and he enrolled instead as a full-time student at the Slade School of Fine Art in Bloomsbury.
Joseph Samuel Moorat (1864–1938) was an accomplished writer of songs, and his music was said to have been the inspiration for much of Woodroffe's work as an illustrator.
1902 was a seminal year for Woodroffe as this was the year that Charles Robert Ashbee's Guild of Handicraft and Essex House Press moved from the East End to Chipping Campden in the Cotswolds where Woodroffe had been a frequent visitor from the mid-1890s when Joseph and Lilian Moorat had acquired a house at Westington, just outside Chipping Campden.
When the Moorats left Westington in 1904, Woodroffe purchased the cottage, employed Ashbee to enlarge and adapt it to include a small studio and he moved into the house in November 1904 and was to live there for more than thirty years.
[7] It was in 1909 that Woodroffe was to receive his most important commission when he was asked to design and make fifteen windows for the Lady Chapel of St Patrick's Cathedral in New York.
Another more unusual commission at this time was to design windows for the private attic chapel of the American actress Mary Anderson, who settled in Court Farm, Worcestershire, after enormous success on the London stage in the 1880s.
In 1935, Woodroffe moved to Jayne's Court, Bisley near Stroud, where he continued to accept commissions for stained glass.