Boro have endured a difficult start to their EFL Championship campaign. They played out a 1-1 draw against West Bromwich Albion in their opening game before falling to a 3-2 defeat at the hands of Queens Park Rangers in their second league outing.
Middlesbrough have won the cup competition once, lifting the title in the 2003-04 campaign. However, they were knocked out in the first round of the tournament in two of the last three seasons and will hope they can avoid a repeat of such this season.
Barnsley were beaten 1-0 by Plymouth Argyle in their first game since their return to League One. However, they bounced back in their next match as they beat Cheltenham Town 1-0 and will be looking to build on that positive result this week.
The Tykes were knocked out by Bolton Wanderers at this stage of the tournament last season, marking their third first-round exit in the last four seasons. They will hope for better luck this time around.
Middlesbrough vs Barnsley Head-to-Head
There have been 66 meetings between Middlesbrough and Barnsley. The hosts have won 34 of those games while the visitors have won 20 times. There have been 12 draws between the two sides.
The two teams last faced off in a league clash earlier this year, with the Tykes winning 3-2.
Middlesbrough Form Guide (All Competitions): L-D-W-L-W
Barnsley Form Guide (All Competitions): W-L-W-D-D
Middlesbrough vs Barnsley Team News
Darragh Lenihan received a red card last time out and has been suspended from the midweek clash. All other players are fit and in contention for selection for manager Chris Wilder.
Suspended: Darragh Lenihan
Nicky Cadden came off injured last time out and is a doubt for this one alongside Matty Wolfe. Michal Helik is injured and will not play on Wednesday.
Injured: Michal Helik
Doubtful: Matty Wolfe, Nicky Cadden
Middlesbrough vs Barnsley Predicted XI
Middlesbrough Predicted XI (3-5-2): Liam Roberts; Anfernee Dijksteel, Dael Fry, Paddy McNair; Tommy Smith, Riley McGree, Matt Crooks, Jonathan Howson, Ryan Giles; Marcus Forss, Chuba Akpom
Barnsley Predicted XI (3-5-2): Bradley Collins; Conor McCarthy, Mads Juel Andersen, Liam Kitching; Jordan Williams, Josh Benson, Luke Thomas, Luca Connell, Callum Styles; Devante Cole, James Norwood
Middlesbrough vs Barnsley Prediction
Boro are on a run of back-to-back winless outings after picking up three wins in their four pre-season games.
Barnsley went unbeaten throughout the off-season and have now lost just one of their last seven games across all competitions.
We are backing the hosts to win this one as they are the stronger side ahead of the midweek game.
Prediction: Middlesbrough 2-1 Barnsley