Cashman was used during his career mostly as a ruckman and forward. He was recruited locally to Fitzroy and kicked 25 goals for them in 1929.
In 1932 he went to Western Australia and took on the role of captain-coach of West Perth, steering them to their first WAFL premiership since 1905 in his first year in charge. He led West Perth to a third place the following season and was lured back to Fitzroy where he was appointed captain-coach.
After just two games as captain-coach of Fitzroy, Cashman resigned, citing that members of the club committee were against him. A four-time VFL interstate representative, he got a clearance to Carlton and finished the season there, kicking 19 goals up forward.
Although he started the 1935 season at Carlton, he ended up at Yarraville and was a centre half forward in their premiership that year. After a year back with West Perth in 1936, he continued his coaching career in 1937 when he was put in charge of Yarraville and in 1938 he became captain-coach of Cananore in Tasmania before retiring in 1941.
^Holmesby, Russell; Main, Jim (2014). The Encyclopedia of AFL Footballers: every AFL/VFL player since 1897 (10th ed.). Melbourne, Victoria: Bas Publishing. p. 138. ISBN978-1-921496-32-5.
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