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versus
September 2014
Tue 23 19:45 Liverpool 2-2 Middlesbrough 1-0 41,857 Round 3 Report
14-13 penalties in progress (1-1 after 90 mins)
August 2014
Tue 26 19:45 Middlesbrough 3-1 Preston North End 0-0 10,727 Round 2 Report
Tue 12 19:45 Oldham Athletic 0-3 Middlesbrough 0-1 4,311 Round 1 Report
August 2013
Tue 6 19:45 Middlesbrough 1-2 Accrington Stanley 1-1 6,774 Round 1 Report
December 2012
Wed 12 19:45 Swansea City 1-0 Middlesbrough 0-0 15,048 Quarter-final Report
October 2012
Tue 30 19:45 Sunderland 0-1 Middlesbrough 0-1 32,535 Round 4 Report
September 2012
Tue 25 19:45 Preston North End 1-3 Middlesbrough 1-2 4,959 Round 3 Report
August 2012
Tue 28 19:45 Gillingham 0-2 Middlesbrough 0-1 5,146 Round 2 Report
Sat 11 15:00 Bury 1-2 Middlesbrough 0-1 2,964 Round 1 Report
September 2011
Tue 20 20:00 Crystal Palace 2-1 Middlesbrough 1-0 5,448 Round 3 Report
August 2011
Wed 24 19:45 Peterborough United 0-2 Middlesbrough 0-2 5,012 Round 2 Report
Tue 9 19:45 Walsall 0-3 Middlesbrough 0-2 3,564 Round 1 Report
August 2010
Tue 24 19:45 Millwall 2-1 Middlesbrough 2-0 6,704 Round 2 Report
Tue 10 19:45 Chesterfield 1-2 Middlesbrough 0-2 6,509 Round 1 Report
August 2009
Tue 25 19:45 Nottingham Forest 2-1 Middlesbrough 8,838 Round 2 Report
After extra time
September 2008
Tue 23 20:00 Manchester United 3-1 Middlesbrough 53,729 Round 3 Report
August 2008
Tue 26 20:00 Middlesbrough 5-1 Yeovil Town 15,651 Round 2 Report
September 2007
Wed 26 20:00 Tottenham Hotspur 2-0 Middlesbrough 32,280 Round 3 Report
August 2007
Wed 29 20:00 Middlesbrough 2-0 Northampton Town 11,686 Round 2 Report
September 2006
Wed 20 20:00 Middlesbrough 0-1 Notts County 11,148 Round 2 Report
December 2005
Wed 21 20:00 Middlesbrough 0-1 Blackburn Rovers 14,710 Round 5 Report
November 2005
Wed 30 20:00 Middlesbrough 2-1 Crystal Palace 10,791 Round 4 Report
October 2005
Wed 26 20:00 Everton 0-1 Middlesbrough 25,844 Round 3 Report
November 2004
Wed 10 20:00 Liverpool 2-0 Middlesbrough 28,176 Round 4 Report
October 2004
Wed 27 20:00 Middlesbrough 3-0 Coventry City 11,833 Round 3 Report
February 2004
Sun 29 14:00 Bolton Wanderers 1-2 Middlesbrough 72,634 Final Report
Tue 3 20:00 Middlesbrough 2-1 Arsenal 28,781 Semi-final L2 Report
January 2004
Wed 28 20:00 Middlesbrough P-P Arsenal Semi-final L2 Report
Tue 20 19:45 Arsenal 0-1 Middlesbrough 31,070 Semi-final Report
December 2003
Wed 17 19:45 Tottenham Hotspur 1-1 Middlesbrough 25,307 Round 5 Report
Wed 3 20:00 Middlesbrough 0-0 Everton 18,568 Round 4 Report
October 2003
Wed 29 20:00 Wigan Athletic 1-2 Middlesbrough 8,046 Round 3 Report
September 2003
Wed 24 20:00 Middlesbrough 1-0 Brighton & Hove Albion 10,435 Round 2 Report
November 2002
Wed 6 19:45 Ipswich Town 3-1 Middlesbrough 14,417 Round 3 Report
October 2002
Tue 1 19:45 Brentford 1-4 Middlesbrough 7,558 Round 2 Report
October 2001
Wed 10 19:45 Blackburn Rovers 2-1 Middlesbrough 9,536 Round 3 Report
September 2001
Tue 11 19:45 Middlesbrough 3-1 Northampton Town 3,915 Round 2 Report