Middlesbrough won this competition in 2004 for their only major honour
Wrexham reached the fourth round of the EFL Cup last season
Recommended bet: FT Draw @ 11/4 with LiveScore Bet
Middlesbrough suffered an agonising defeat in the Championship play-off final last season, failing to take advantage of their reprieve following Southampton's expulsion.
As such, Boro face another season of second tier football, but before the league campaign begins, Wrexham are the visitors to the Riverside for this EFL Cup first round clash.
The Red Dragons reached the fourth round of this competition last season, before losing narrowly 2-1 to Cardiff City and hopes will be high for a similar sort of run this term.
The latest Middlesbrough vs Wrexham odds are available on LiveScore Bet
Team news
Boro have lost Hayden Hackney and Dael Fry this summer, but new arrivals include Will Lankshear, Jeremy Sarmiento and Kyle Joseph, who will all be eager to impress in the first competitive game of the new season.
Dragons boss Phil Parkinson has made two summer signings so far, bringing in defender Danny Imray from Crystal Palace and midfielder Ben Whiteman from Preston North End, with the former likely to start on Friday evening.
The stats
Boro failed to win any of their three pre-season friendlies, drawing with both Celtic and Espanyol, with a defeat to Huddersfield Town sandwiched in between.
Wrexham's pre-season was more productive, with victories over Manchester United and Leeds United ending their preparations following narrow losses to Liverpool and Sunderland.
Both meetings between the two sides last season finished as draws. At the Riverside in October, a late goal by Hackney secured a point for the home side.
At the Racecourse Ground in May, four goals were scored in the first half and the game eventually finished 2-2.
Boro drew four of their last seven regular Championship matches last season, while Wrexham drew two of their final seven league games.
By reaching the fourth round of the EFL Cup last term, Wrexham achieved their best run since reaching the quarter-finals in 1977/78.
Boro have progressed beyond round two of the tournament only once in the previous seven seasons, exiting at the semi-final stage during the 2023/24 season.
The latest Middlesbrough vs Wrexham odds are available on LiveScore Bet
Prediction
Kim Hellberg will still have the play-off defeat in the back of his mind entering the 2026/27 campaign, but, despite that, Boro start as one of the favourites to seal promotion to the Premier League.
This EFL Cup clash will be ideal preparation for the Championship season kicking off next week and, while this competition is not the main priority, a victory at the Riverside would build momentum ahead of their league opener against Lincoln City.
Parkinson led his Dragons side to a seventh place finish last term, missing out on the play-offs by just two points.
Again, like Boro, this cup will not be the priority. A solid showing away from home, however, would likely give the Welshmen a confidence boost.
This should be a tight affair and backing a full-time draw offers excellent value, especially considering both league games last season finished with the spoils being shared.
Prediction: Middlesbrough 1-1 Wrexham (5/1 with LiveScore Bet)
