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As a collector of football medals there is an unusual thing on the inscription. It actually gives the date which I have never come across before but also the word 'to' again is most unusual. April suggests it may have been a cup final but normally it would just have the name of the recipient plus his club and the year so could it be that it was presented by his club for services rendered?
He would be about 17 and it is possible his voice had broken and he was leaving the choir or in fact joining the men.
Not really much help to you but thought I would pass on those observations. A local newspaper of the day may supply the answers as many did include local football results at that time.

Many thanks rosie99, very much appreciated.

No, the one I am looking for was an Elizabeth Aires of Fenny Compton, born 1814, who married James Grubb at Hellidon in 1935. James died in 1847 aged just 44 and in 1852 Elizabeth gave birth to a base born child named Thomas Francis. I have found no further trace of Elizabeth.
They left six children, some lived in Neithrop in Banbury including Oliver who was later a wheelwright in Fenny Compton. He took over the house (still Extant) of his brother William when the latter moved to Leicester.
There were other Grubbs in FC earlier but the wheelwright line is from my family in Hellidon.

I have been to the village and seen the cottage also took a photo of the gravestone. I trust you have been into the church and seen the notice on the bier on which it relates that the straps were made and donated by Oliver Grubb and two of his sons subscribed to them?
Hellidon, where the family came from after moving from Daventry is worth going to, William Grubb the Butcher there married Ann Aris the Millers daughter and your line came from them.
I have a document from 1814 with William's signature on it and also copies of his will.
I have traced back to the 1500s, my DNA suggests we were originally Danish Vikings who came and settled in Northamptonshire in the 1100s.