Bolton were 1-0 winners over Barrow in the first round of the EFL Cup on August 8, but they face a step-up in class in the second round of the competition, preparing to welcome Boro.
The Trotters have never won the League Cup, but they have made the final on two previous occasions, including in 2003-04, suffering a 2-1 defeat to Middlesbrough in Cardiff.
Ian Evatt’s side have made a strong start to their League One campaign, picking up 10 points from their opening five matches, which has left them in third position in the table, two points behind the leaders Oxford United.
Bolton’s main focus for this season will be to earn promotion back to the Championship, but a cup run is always good for confidence, and the League One side will want to prove that they can compete with second-tier opposition in Tuesday evening’s affair.
The Trotters have lost each of their last eight matches against Boro in all competitions, though, including a 2-0 defeat when the two teams last locked horns in the Championship in April 2019.
Middlesbrough were so impressive in the Championship last season under Michael Carrick, ultimately finishing fourth in the table, losing to Coventry City in the semi-finals.
Boro would have been looking to go again this season, but it has been an underwhelming start, picking up just one point from their opening four matches to sit down in 22nd position in the division
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Carrick’s side will enter this match off the back of a 4-2 defeat at West Bromwich Albion on Saturday, while they have been beaten in three of their five games in all competitions this season.
Boro’s sole victory this term came against Huddersfield Town in the last round of this particular competition, recording a 3-2 win to progress into the second round.
The 2003-04 League Cup winners have not lost to Bolton in any competition for more than 10 years, including eight wins in a row against their opponents on Tuesday night, with all of those matches taking place in the second tier of English football.
