The Sad Passing of War Hero Roy Ollerhead

Roy Ollerhead, 3rd row from front, 6th from right
Roy Ollerhead OO (1934-1940)
As ever the School and Old Oswestrian society saddened to learn of the passing of an OO. Roy Ollerhead passed away at the age of 88 and was not only a localhero , but a war hero. Roy was a retired RAF navigator who flew 30 bombing missions over Germany before later teaching hundreds of schoolchildren in Oswestry.
Roy Ollerhead, born and raised in Oswestry, spending most of his life living on Salop Road. He was educated at Oswestry School where he was an enthusiastic and natural sportsman, where he enjoyed cricket and football. His grandson Barry Richards OO (1993) believes how this passion has passed down the generations as he too enjoyed sports whilst at School.![]()
Roy Ollerhead, Front Row, second from right
After School, at the age of 18, Roy joined the RAF. His planned destination was a prestigious place at Cambridge University due to the outbreak of the Second World War, destiny intervened. To complete his training tt was not unheard of for Roy to cycle daily to RAF Shawbury, a 90-minute trip.
Roy’s daughter Carole, described how Roy was eager to become a pilot but “it soon became apparent to a very white faced instructor, who had been subject to a hair-raising spiral dive over the Humber River, that it might be safer for everyone if he chose a different role!” However Roy wasn’t to be disappointed for long as he found his forte in Navigation where he could apply his mathematic skills.
Roy was stationed at several bases throughout England and Wales, including RAF Wicknenby, where he joined 626 Squdron of Lancaster Bombers. It is with this squadron Roy flew 30 missions over Nazi Germany, which is a remarkable feat as the average mission number was three. Roy was eventually awarded the Distinguished Flying Medal in 1944 by King George VI.
This squadron never had their group picture taken due to fear of superstition. However, this was righted fifty years later when Roy tirelessly searched for his lost crew to celebrate their reunion. His daughter said: “He enjoyed his war years although always realised how lucky he was to return home. He always thought about the whereabouts of his six crew. In retirement he managed to contact all but one of the crew and their first reunion, in Oswestry in 1993, was a very emotional occasion.” Roy’s chapter in ‘God Bless the Prince of Wales’ is a very passionate account of his time at war.
After the war Roy retired from the RAF and trained in a new career as a primary school teacher. He returned to Oswestry School’s classroom do complete his training. Roy had been presented a fountain pen by the School, which unfortunately got damaged by an enthusiastic pupil throwing a board rubber. Roy went on to teach a t the Orthopaedic where he taught his classes outside, where patients were wheeled out on their beds for the lessons. Roy’s final teaching post was at Woodside School, where he taught until he retired in 1982.
Roy never approached retirement with a thought of relaxation as he spent many years tracing he old crew, played a part at Oswestry Football club, and spending time with his family.
Roy leaves three daughters, five grandchildren and seven great-grandchildren but is rejoining his wife Maureen of 67 years marriage, who passed away in April 2011.
The School and OO Society extend our sympathies to Roy’s family and friends.
