Background
Cummings grew up a Hearts fan and attended Tynecastle High School playing for local boys team Hutchison Vale before joining Hearts, after struggling with injuries he was released by Hearts in 2012.
Cummings grew up a Hearts fan and attended Tynecastle High School playing for local boys team Hutchison Vale before joining Hearts, after struggling with injuries he was released by Hearts in 2012.
After an impressive season with Hutchison Vale he was signed by Hibernian in summer 2013. Cummings made his debut senior appearance for Hibernian in a Scottish Premiership match against Inverness Caledonian Thistle in November 2013. However, Cummings missed in the penalty shootout after Hibs lost the return leg 2–0 and were relegated to the Scottish Championship.
Cummings scored his first career goals on 21 May 2014, netting twice as Hibernian won 2–0 against Hamilton Academical in the first leg of the Scottish Premiership Play-offs. Cummings won the SPFL young player of the month award for September 2014, after his two goals helped Hibs to beat Rangers in Glasgow.