Football
Oxford vs Middlesbrough Preview: Odds, Tips and Prediction
Date: 22 November 2025 Venue: Kassam Stadium SportsBoom previews the Championship clash between Oxford and Middlesbrough on Saturday, November 22, 2025. Those who follow the Championship closely should head over to the top English National League football betting sites for the latest odds movements. We’ve provided a full Oxford vs Middlesbrough preview to keep you in the loop of potential talking points.
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Hayden Hackney / Getty Images
Promotion-chasing Middlesbrough are on the road, and they will be keenly aware that Stoke and Preston are breathing down their necks. Currently second, Middlesbrough have picked up just one win from their past four games. In stark contrast, Oxford are languishing just above the relegation zone, but they have generally wilted against Middlesbrough, and last season, they were thumped 6-2 at home.
Pre-Game Odds and Win Probability: Middlesbrough Much Fancied
We’ve located some pre-match betting odds from one of the most reputable online sports betting operators to see how things stack up.
Home: 14/5 (3.80) – 26.3%
Draw: 12/5 (3.40) – 29.4%
Away: 1/1 (2.00) – 50%
*Odds courtesy of BetUK, subject to change
Head-to-Head Record
Last Five Meetings (English National League)
To inform our Oxford vs Middlesbrough predictions, we’ve revealed the tale of the tape between the two sides:
29/03/25: Middlesbrough 2-1 Oxford
23/11/24: Oxford 2-6 Middlesbrough
03/05/98: Middlesbrough 4-1 Oxford
21/10/97: Oxford 1-4 Middlesbrough
09/04/94: Middlesbrough 2-1 Oxford
Oxford Current Form - LWDLL
Oxford boss Gary Rowlett has come under increased scrutiny. After a 2-1 win away to Sheffield Wednesday at the end of October, the U’s have only picked up a solitary point from their past three Championship outings.
Currently 21st in the table, and just three points above the relegation zone, Oxford have crucial games coming up against teams around them, such as Norwich and Swansea, as they seek to keep themselves afloat.
Oxford crashed to a 6-2 defeat to Middlesbrough in the corresponding fixture last term, and they have been leaky at the back this season, conceding 22 times.
Middlesbrough have been Oxford’s bogey team, but this will be only the third Championship meeting between these two sides. Oxford haven’t beaten Middlesbrough at home since a 3-1 win over 35 years ago in the old Division 1.
Key Players to Watch
- Will Lankshear
Currently on loan from Tottenham, Will Lankshear has been a bright spark for Oxford. While he’s often been on the losing side, he’s netted five times in the league this term with a decent expected goals rate (xG) of 3.7. - Brian De Keersmaecker
Although injury disrupted the start of his Oxford career, Brian De Keersmaecker is starting to flourish. One of his best performances came in the 3-1 win over Bristol City in September, and he has weighed in with three assists this season, underlining his importance to the cause. - Cameron Brannagan
An Oxford veteran, Cameron Brannagan is the club’s captain, and he has set the standards with his masterful displays. He’s scored twice in his past four league outings, and Middlesbrough will need to keep close tabs on him.
Oxford Team News
Oxford have no fresh injury worries ahead of their clash with Middlesbrough, and they were given a big boost when defender Ciaron Brown returned to action after six months out with a knee problem.
Middlesbrough Current Form – WDLDW
After a recent wobble, Middlesbrough returned to winning ways with a 2-1 win at home to Birmingham. The departure of head coach Rob Edwards to Wolves will, of course, provide some uncertainty, but Adi Viveash has taken over the reins in the meantime.
It had been a bit of a turbulent week after a 3-0 thrashing away to Watford, and Middlesbrough can’t afford to let table toppers Coventry pull further away.
A victory over Oxford will be vital, and as past encounters have shown, Middlesbrough have had a vice-like grip on this fixture.
Key Players to Watch
- Hayden Hackney
Despite the recent unrest, Hayden Hackney has been a reassuring presence. A fabulous box-to-box midfielder, Hackney has been attracting interest ahead of the January transfer window, and he’s scored twice in his past four league outings. He’s one to watch out for. - Luke Ayling
An experienced defender, Luke Ayling is a physical presence and is great in the air. The only worry is that he’s been cautioned three times this season, meaning he needs to keep his cool to avoid a suspension over the coming weeks. - Tommy Conway
Two goals might be a paltry return for Tommy Conway given his quality, but his high-energy style and ability to drift in from the left could give Oxford problems.
Middlesbrough Team News
George Edmundson should return after missing the Birmingham game through illness, and while Middlesbrough were short of defensive options, Dael Fry and Matt Targett pushed themselves through the pain barrier. The pair came off injured, but they will be assessed before Oxford, and they should be fit to play.
Predicted Line-Ups
Oxford: 4-5-1
Cumming; Long, Brown, Helik, Brown, Leigh, Vaulks, Brannagan, Mills, De Keersmaecker, KrasstevMiddlesbrough: 4-5-1
Brynn, Brittain, Ayling, Jones, Targett, Morris, Browne, McGree, Hackney, Whittaker, Conway
Suggested Bets
We’ve picked out some odds from several reputable English National League football sportsbooks to influence your betting strategies.
Over 2.5 Goals: In each of the past five meetings, at least three goals have been hit, so we could be in for a barnstormer. English National League sportsbooks seem to think so. (20/21 with Quinn Bet)
Middlesbrough to Win Either Half: Middlesbrough will look to impose themselves early on, and they could put Oxford to the sword. Boro to win either half holds value. (8/15 with Fitzdares)
Over 9.5 Corners: The past two clashes have seen plenty of corners awarded, with a combined average of 15. Over 9.5 corners could be worth exploring further. (3/5 with Betway)
Value Bets
Middlesbrough to Score in Both Halves: Middlesbrough have been strong starters, but they have also finished games well, so this line is worth a punt. (21/10 with Bet442)
Tommy Conway – Anytime Scorer: Although he’s only netted twice this season, he was on target when Middlesbrough last visited the Kassam Stadium, and there is value in this line. (17/10 with Leovegas)
First Team to Score – Oxford: Although Oxford has struggled this term, they have netted the opening goal in this fixture in the past two meetings, so this line shouldn’t be ignored. (71/50 with All British Casino)
Prediction: Middlesbrough to Win and Both Teams to Score
Middlesbrough have bullied Oxford at times, with their 6-2 win last season paying testament to this. Despite the distraction of head coach Edwards leaving and moving to Wolves, Middlesbrough’s turbulence off the field pales into insignificance when you consider Oxford is entrenched in a relegation battle. This could be an entertaining match, and one where Middlesbrough come out on top, with both sides finding the net.
Charles Perrin is a highly experienced sports betting content writer with over six years of working with some of the leading sportsbooks in the UK, including bet365 and William Hill.