In the early twentieth century, one of the main ways the Teesside faithful kept up to date with developments at Ayresome Park was through the rich array of cartoons and caricatures produced by celebrated illustrators of the day.

These creative and often humorous spins on the football world depicted match action and life around the club including controversial incidents, record-breaking transfers and the occasional promotion. These entertaining perspectives on Ayresome life were staple features of matchday programmes and local press coverage for decades and their influence remains in today’s football cartoonists.

One of the most notable artists to portray life at Ayresome Park was Fred May, famed for his illustrations of life on the Western Front and caricatures of leading society figures and senior politicians including Sir Winston Churchill. May’s work regularly appeared in Boro’s Key Card match programmes, including the examples found in Art of Ayresome which preview the opening home fixture of the 1912/1913 campaign and review key moments from a home draw with Tottenham Hotspur later that season. Such was the popularity of May’s work that an exhibition of his cartoons at Middlesbrough Central Library in 1930 attracted thousands of visitors.

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Those wishing to view Fred May’s work today can see many examples in the National Portrait Gallery.