He was born in London on 30 July 1847, eldest son of Charles James Cruttwell, barrister-at-law, of the Inner Temple, and his wife Elizabeth Anne, daughter of Admiral Thomas Sanders.
Educated under James Augustus Hessey at Merchant Taylors' School, London (1861–6), he went on with a foundation scholarship to St John's College, Oxford, in 1866.
A few months later he was appointed rector of Denton, Norfolk, and in 1891 he accepted from Merton College the benefice of Kibworth-Beauchamp in succession to Edmund Knox.
While at Kibworth he was also rector of Smeeton-Westerby, Leicestershire (1891–4), rural dean of Gartree (1892–1902), examining chaplain to the bishop of Peterborough (1900), and proctor in convocation (1900).
[1] In 1901 Cruttwell was nominated by Lord Salisbury to the crown benefice of Ewelme, Oxfordshire, and in 1903 he was collated by the bishop of Peterborough to a residential canonry.