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Plymouth Argyle v Middlesbrough FC 05.09.1959
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Hull City v Middlesbrough FC 09.09.1959
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Grimsby Town v Middlesbrough 31.10.1959
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Leyton Orient v Middlesbrough 31.10.1959
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Huddersfield Town v Middlesbrough FC 07.11.1959
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Bristol Rovers v Middlesbrough FC 21.11.1959
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Brighton and Hove A v Middlesbrough FC 05.12.1959
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Rotherham United v Middlesbrough 26.12.1959
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Derby County v Middlesbrough FC 02.01.1960
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Bristol City v Middlesbrough FC 13.02.1960
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Aston Villa v Middlesbrough FC 05.03.1960
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Barrow v Middlesbrough FC 12.03.1960
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Peterborough United v Middlesbrough 14.03.1960
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Huddersfield Town v Middlesbrough 26.03.1960
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Sheffield United v Middlesbrough FC 18.04.1960
