Crawley served briefly as an officer in the British army before marrying Constance Thompson in 1892 in England. As their careers took separate directions, Constance and Sayre separated, with Constance eventually moving to Los Angeles where she starred in several silent films, and Sayre continuing his acting career in New York City. Although he continued in Broadway productions during the 1920s and 1930s, sometimes sharing the stage with Mary Ward, Sayre also did Shakespeare plays at the Garden Theatre, starring opposite Sybil Thorndike, Sydney Greenstreet and others
He was also a charter member with Eva Le Gallienne"s Civic Repertory Theatre.
When he died on 7 March 1948 in New York, his obituary in The New York Times noted that he had "devoted his career to the New York stage since the turn of the century."
Thorndike refers to Crawley in her letters as "Master Rawdon", after the character Rawdon Crawley in Vanity Fair, and writes that she and others looked up to him as an older brother. Everyman (1902–1903)
Twelfth Night (1904, 1912–1913, 1919, 1920, 1926)
Romeo and Juliet (1910, 1923, 1930)
Hamlet (1913, 1919, 1920)
The Cherry Orchard (1923, 1928, 1933)
Or, the Boy Who Wouldn"t Grow Up (1928)
Hedda Gabler (1928)
The Would-Be Gentleman (1932)
Alice in Wonderland (1932. Adapted by Eva Le Gallienne)
The Corn Is Green (1940–1942)
The Late George Apley (1944–1945).