Papers relating to Woolley's service in Ceylon (now Sri Lanka), Jamaica, Cyprus and British Guiana (now Guyana). Included are:
- Papers concerning the visit by the Duke of Gloucester to Ceylon in 1934 and an earlier visit by the Duke and other officials
- Cuttings from West Indian newspapers, including accounts of the 'New Deal' for Jamaica introduced by Woolley (a land settlement scheme, involving Government expenditure of half a million pounds, to help labourers and the unemployed)
- Drafts and notes for speeches and broadcasts delivered by Woolley
- Cuttings about Winston Churchill's visit to Cyprus in February 1943, and the Knighthood subsequently conferred on Woolley
- Correspondence, including letters from Arthur Creech Jones, Sir Gordon Lethem, Sir George Gater, Sir Hugh Foot and Lord Winster
- Cuttings from British Guianan newspapers
There is little material in the collection relating to Woolley's time as Chief Secretary in Nigeria. References in the correspondence about his move to Cyprus suggest that wartime conditions may have necessitated the abandonment of relevant papers.