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Liverpool kick off their Capital One Cup campaign with a third-round tie against Middlesbrough at Anfield.
The teams have not met since February 2009 when the Reds went down to a 2-0 Premier League defeat at the Riverside Stadium.
Middlesbrough's last visit to Anfield came earlier in that 2008-09 season when late goals from Jamie Carragher and Steven Gerrard secured a 2-1 win for Liverpool.
The last time the sides went head to head in the League Cup was November 2004. Two late goals from Neil Mellor sealed a 2-0 win for Liverpool at Anfield.