Throughout his career Douglas attracted commissions from wealthy and important patrons. His first-known independent work was an ornament, which is no longer in existence, for the garden of the Honourable Mrs Cholmondeley. She was the sister-in-law of Hugh Cholmondeley, 2nd Baron Delamere, and it was from the 2nd Baron that Douglas received his first major commission, a considerable rebuilding of the south wing of his seat at Vale Royal Abbey in 1860. Around the same time, Lord Delamere commissioned him to build the church of St John the Evangelist at Over, Winsford, as a memorial to his first wife.