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Wilkinson contributed articles on military matters for the Liberal-supporting newspaper The Manchester Guardian from 1881 until 1892, when C.P. Scott decided Wilkinson had to go because of his "lack of a real hold of Liberal principles". He then wrote for the Tory-supporting paper The Morning Post until 1914.
In 1909 he was elected to a fellowship of All Souls, University of Oxford, and became the first Chichele Professor of Military History at Oxford. He retired from Oxford in 1923.