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| Middlesbrough FC v Reading FC 27/04/2019 | View match | |
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| Luton Town FC v Middlesbrough FC 02/08/2019 | £6.75 | |
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| Blackburn Rovers FC v Middlesbrough FC 17/08/2019 | View match | |
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| Middlesbrough FC v Millwall FC 24/08/2019 | £9.99 | |
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| Cardiff City FC v Middlesbrough FC 21/09/2019 | £7.50 |