Boland was educated at two private Catholic schools, one Irish, the second English, and both of whose existence and evolution were influenced by John Henry (later Cardinal) Newman – the Catholic University School, Dublin, and The Oratory School, Birmingham (since re-located to near Reading) where he became head boy. His secondary education in the two schools either side of the Irish Sea helped give him the foundation and understanding to play an influential role in the politics of Great Britain and Ireland at the beginning of the 20th century, when he was a member of the Irish Parliamentary Party which pursued constitutional Home Rule.