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Chelsea v Manchester United 23.08.1958
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Nottingham Forest v Manchester United 27.08.1958
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Blackpool FC v Manchester United 30.08.1958
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Nottingham Forest v Manchester United 03.09.1958
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Blackburn Rovers v Manchester United 06.09.1958
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West Ham United v Manchester United 08.09.1958
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Newcastle United v Manchester United 13.09.1958
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Manchester United v West Ham United 17.09.1958
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Tottenham Hotspur v Manchester United 20.09.1958
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Manchester United v Manchester City 27.09.1958
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Manchester United v BSC Young Boys 01.10.1958
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Wolverhampton Wanderers v Manchester United 04.10.1958
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Manchester United v Aston Villa Reserves 04.10.1958
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Preston North End v Manchester United 08.10.1958
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Manchester United v Arsenal 11.10.1958
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Everton v Manchester United 18.10.1958
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Manchester United v West Bromwich Albion 25.10.1958
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Leeds United v Manchester United 01.11.1958
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Burney v Manchester United 08.11.1958
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Sheffield Wednesday Reserves v Manchester United 15.11.1958
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Bolton Wanderers v Manchester United 15.11.1958
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Manchester United v Luton Town 22.11.1958
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Birmingham City v Manchester United 29.11.1958
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Burnley Reserves v Manchester United Reserves 29.11.1958
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Manchester United v Leicester City 06.12.1958
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Preston North End v Manchester United 13.12.1958
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Chelsea v Manchester United 20.12.1958
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Manchester United v Aston Villa 26.12.1958
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Aston Villa v Manchester United 27.12.1958
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Blackpool v Manchester United 03.01.1959
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Norwich City v Manchester United 10.01.1959 | FA Cup
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Blackburn Rovers FC v Manchester United 17.01.1959 | Postponed
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Swansea Town v Manchester United 24.01.1959
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Man Utd Reserves v Notts County Reserves 24.01.1959
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Newcastle United v Manchester United 31.01.1959
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Tottenham Hotspur v Manchester United 07.02.1959
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Manchester United v Wiener Sport Club 11.02.1959
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Manchester United v Manchester City 14.02.1959
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Wolverhampton Wanderers v Manchester United 21.02.1959
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Arsenal v Manchester United 28.02.1959
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Blackburn Rovers v Manchester United 02.03.1959
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Everton v Manchester United 07.03.1959
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Manchester United v West Bromwich Albion 14.03.1959
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Derby County Reserves v Manchester United Reserves 14.03.1959
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Leeds United v Manchester United 21.03.1959
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Portsmouth v Manchester United 27.03.1959
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Burnley v Manchester United 28.03.1959
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Portsmouth FC v Manchester United 30.03.1959
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Bolton Wanderers v Manchester United 04.04.1959
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Luton Town v Manchester United 11.04.1959
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Manchester City v Manchester United 13.04.1959 | Senior Cup Final
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Manchester United Youth v Blackburn Rovers Youth 15.04.1959 | Youth Cup Semi Final 2nd Leg
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Birmingham City v Manchester United 18.04.1959
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Leicester City v Manchester United 25.04.1959
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Feyenoord v Manchester United 28.04.1959 | Reserves
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Bishop Auckland v Manchester United 30.04.1959