Boro will enter the match off the back of a 4-2 defeat at West Bromwich Albion in the second tier on Saturday, while Bolton drew 1-1 with Burton Albion in the League One on the same afternoon.
Match preview
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 not 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.
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.
Bolton Wanderers EFL Cup form:
W
Bolton Wanderers form (all competitions):
Middlesbrough EFL Cup form:
W
Middlesbrough form (all competitions):
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Team News
Bolton boss Evatt will ring the changes from the side that took to the field for Saturday's 1-1 draw with Burton Albion.
Cameron Jerome is set to come into the side in the final third of the field, while Carlos Gomes and Dan Nlundulu should also be introduced into the XI.
Will Forrester was a half-time substitute against Burton on Saturday, and the 22-year-old is also expected to be among the players to earn starts for Tuesday's second-round affair.
Boro, meanwhile, will be missing Anfernee Dijksteel through injury; Tommy Smith will also be absent due to the red card that he picked up against West Brom in the league on Saturday.
Like Bolton, there will be wholesale changes in the away side's XI, with Paddy McNair, Isaiah Jones and Dan Barlaser among those likely to be introduced.
Carrick will be determined to return to winning ways, though, so it would not be a surprise to see Darragh Lenihan and Sam Silvera retain their starting roles from the weekend.
Bolton Wanderers possible starting lineup:
Coleman; Forrester, Ricardo, Iredale; Dacres-Cogley, Maghoma, Thomason, Ashworth; Nlundulu, Jerome, Gomes
Middlesbrough possible starting lineup:
Glover; McNair, Van den Berg, Lenihan, Coulson; Payero, Barlaser, Hackney; Jones, Rogers, Silvera
We say: Bolton Wanderers 1-2 Middlesbrough
This is a difficult match to call, as both managers will make a number of changes. Bolton have certainly enjoyed the stronger start to the campaign, but we believe that Boro's superior quality will allow them to progress to the third round of the competition.