On his return from South Africa, Simpson joined Richmond Rugby Club, and in 1893 was selected to play for invitational touring team, the Barbarians.
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Simpson first came to note as a rugby player when he was chosen to represent Cambridge University; and earned a single sporting 'Blue' as part of the Cambridge team in The Varsity Match of 1890.
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He received his Bachelor of Arts in 1891, and in 1896 was admitted as a solicitor.
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