"The Winslow Boy" is set against the backdrop of great social upheaval in Great Britain, as women began turning to increasingly militant methods in their struggle for the vote. In 1889, Emmeline Pankhurst helped found the Woman's Franchise League, which secured a woman's right to vote in local elections five years after its founding. Pankhurst then had a hand in creating The Women's Social & Political Union in Manchester in 1903. This group gained recognition when Pankhurst moved its headquarters to London and began holding public meetings, and led protest marches. Then the Women's Social & Political Union initiated a militant campaign for the vote. In 1910, a new bill which would have given one million women the vote passed through Parliament, but was vetoed by Prime Minister Asquith.

Following the veto, the Suffragette issue became more violent on all sides. Though Catherine Winslow was more demure in her approach, other women resorted to breaking windows, chaining themselves to post boxes, and throwing themselves in front of horses to prove their dedication. This type of demonstration was most evident on "Black Friday," where women who were demonstrating at Parliament were abused and beaten by police. The suffragettes who were imprisoned turned to hunger strikes, and were eventually force fed by authorities. Reginald McKenna, now the British Home Secretary, then introduced the Cat and Mouse acts so that suffragettes could be released and rearrested to placate an angry public.

In 1928, eighteen years after the time that "The Winslow Boy" is set, British women were finally granted full voting rights.
The Suffragettes