Two Cup Finals lost, 3 points deducted and relegation.
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Middlesbrough v Billingham Town 17.07.1996 - Friendly
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Middlesbrough 11 v Wendleydale League 11 17.07.1996 - Friendly
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Middlesbrough v Crook Town 17.07.1996 - Friendly
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Middlesbrough v North Shields 19.07.1996 - Friendly
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Middlesbrough v RTM Newcastle 27.07.1996 - Friendly
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Middlesbrough v York City 31.07.1996 - Friendly
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Middlesbrough v Parma 03.08.1996 - Friendly
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Middlesbrough v Modena 03.08.1996 - Friendly
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Middlesbrough v Inter Milan 11.08.1996 - Willie Maddsen Testimonial
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Middlesbrough v Billingham Synthonia 14.08.1996 - Friendly
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Middlesbrough v Liverpool 17.08.1996 - Ravenelli scores 3
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Middlesbrough v Chelsea 21.08.1996
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Middlesbrough v Notts Forest 24.08.1996
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Middlesbrough v West Ham 04.09.1996
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Middlesbrough v Coventry 07.09.1996
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Middlesbrough v Everton 14.09.1996
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Middlesbrough v Rep of Ireland 11 15.09.1996 - Bernie Slaven Testimonial
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Middlesbrough v Hereford 18.09.1996 - League Cup 2nd Round 1st Leg
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Middlesbrough v Arsenal 21.09.1996
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Middlesbrough v Hereford 24.09.1996 - League Cup 2nd Round 2nd Leg
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Middlesbrough v Southampton 28.09.1996
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Middlesbrough v Sunderland 14.10.1996
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Middlesbrough v Spurs 19.10.1996
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Norton and Stokton Ancients v Middlesbrough 21.10.1996
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Middlesbrough v Huddersfield 23.10.1996 - League Cup 3rd Round
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Middlesbrough v Wimbledon 26.10.1996
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Middlesbrough v Newcastle 03.11.1996
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Middlesbrough v Dublin City Select 11.11.1996 - Friendly
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Middlesbrough Reserves v Sunderland Reserves 13.11.1996
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Middlesbrough v Derby 17.11.1996
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Middlesbrough v Man Utd 23.11.1996
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Middlesbrough v Newcastle 27.11.1996 - League Cup 27.11.1996
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Middlesbrough v Aston Villa 30.11.1996
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Middlesbrough v Leicester 03.12.1996
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Middlesbrough v Leeds 07.12.1996
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Ponteland v Middlesbrough A 07.12.1996
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Middlesbrough v Liverpool 14.12.1996
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Middlesbrough v Blackburn 21.12.1996 - Postponed
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Blackburn v Middlesbrough 21.12.1996 (postponed) Ticket
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Middlesbrough v Everton 26.12.1996
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Middlesbrough v Coventry 28.12.1996
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Middlesbrough v Arsenal 01.01.1997
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Middlesbrough v Chester City 04.01.1997 - FA Cup 3rd Round
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Middlesbrough v Liverpool 08.01.1997 - League Cup 5th Round
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Middlesbrough v Southampton 11.01.1997
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Middlesbrough v Sheff Wed 18.01.1997
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Middlesbrough v Sheff Wed 18.01.1997
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Middlesbrough v Hednesford 25.01.1997 - FA Cup 4th Round
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Middlesbrough v Wimbledon 01.02.1997
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Middlesbrough v Man City 15.02.1997 - FA Cup 5th Round
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Middlesbrough v Stockport 26.02.1997 - League Cup Semi Final 1st Leg
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Middlesbrough v Newcastle 22.02.1997
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Middlesbrough v Sheff Wed 01.03.1997
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Middlesbrough v Derby 05.03.1997
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Middlesbrough v Derby 08.03.1997 - FA Cup 6th Round
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Middlesbrough v Stockton 11.03.1997 - postponed and never played
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Middlesbrough v Stockport 12.03.1997 - League Cup Semi Final 2nd Leg
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Middlesbrough v Leicester 15.03.1997
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Middlesbrough v Blackburn 19.03.1997
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Middlesbrough v Chelsea 22.03.1997
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Middlesbrough v Notts Forest 24.03.1997
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Middlesbrough v West Ham 09.04.1997
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Middlesbrough v Chesterfield 13.04.1997 - FA Cup Semi Final
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Middlesbrough v Leicester 06.04.1997 - League Cup Final
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Middlesbrough v Sunderland 19.04.1997
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Middlesbrough v Leicester 16.04.1997 - League Cup Final Replay
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Middlesbrough v Chesterfield 22.04.1997 - FA Cup Semi Final Replay
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Middlesbrough v Spurs 24.04.1997
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Middlesbrough v Aston Villa 03.05.1997
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Middlesbrough v Man Utd 05.05.1997
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Middlesbrough v Blackburn 08.05.1997
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Middlesbrough v Chelsea 17.05.1997 - FA Cup Final
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Middlesbrough v Leeds 11.05.1997
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Middlesbrough v Chelsea 17.05.1997 - FA Cup Final
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Middlesbrough v Yeovil 20.05.1997 - Friendly