Photo one is of a chap called Bill Bowker holding the Furness cup. I can find no other information other than his name on the back of the photo stating he is holding the Furness Cup.
Photo two simply states Windsor Street School football team. A school I know to be in Haverton Hill but no date, and also no names. Perhaps your wider, more knowledgeable audience may have some answers?
Photo and details courtesy of Neil Cushin.
Picture Stockton Archive 
Midtown 2nd right, John Lewis (my uncle) front row right Barrie Pierce ( lived in Hawke Street)
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Billy Bowker & his family were neighbours of ours in Belasis Avenue. I remember they emigrated to Australia in the 50’s.
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Littlewoods took over the sponsorship of the Football League Cup in 1986 and, somehow, acquired the trophy in the picture as the new cup to be awarded to the winners. The trophy had originally been used decades earlier as the trophy for the inter-departmental football competition at Furness Shipyard, Haverton Hill.-from the littlewoods cup website
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Hmmm, this doesn’t look like the trophy with the same story shown here:
https://picturestocktonarchive.com/2017/01/16/john-robert-hamilton-with-the-littlewoods-challenge-cup-c1986/
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Mr Harry Taylor was a teacher at Haverton Hill school, he taught my Brother Keith. He lived over the road to us at Corfe Crescent Billingham.
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i am sure that furness cup became the littlewoods cup (or one of its incarnations/sponsors named cup
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I started at Richard Hind in 1957, he was the Religious Knowledge teacher at the School then so it’s before 1957.
He also looked after the senior football team made up from 5th year pupils,
I previously posted a picture of this team taken when I was a player.
Alan Rowbotham
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The shipbuilding firm of Furness Withey had an annual inter-departmental football competition.
The competition ran from about 1889 to 1968, just before the company closed. The winner of the competition was awarded the Viscountess Furness Football Cup. Some years later the trophy was competed for nationally, when it was renamed the Littlewoods Cup. The trophy can be seen on Picture Stockton at https://picturestocktonarchive.com/2017/01/16/john-robert-hamilton-with-the-littlewoods-challenge-cup-c1986/
BUT that trophy is totally different to the one being held by Bill Bowker in the above photo.
Was there another Furness Trophy for football on Teesside, or is the trophy from a different part of the country?
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The teacher in the photograph i would say is Mr Taylor who was a teacher at Richard Hind when I attended bet 1962 & 1967. He seems to be wearing similar clothes in the Richard Hind photographs which may help to date the picture. Dennis Brewer
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