Middlesbrough vs Chelsea Predictions and Picks: Middlesbrough Go Down Swinging

This Tuesday sees Middlesbrough vs. Chelsea in the first of two Carabao Cup games this week. 

Middlesbrough are the only non-Premier League team left and are major underdogs, but can they pull off an upset at home to Chelsea?

Don’t miss our Middlesbrough vs Chelsea tips and predictions on Tuesday, January 9.

Middlesbrough vs Chelsea best odds

Odds courtesy of TonyBet on January 7, 2024.

Middlesbrough vs Chelsea picks and predictions

It’s time for the Carabao Cup to reach the semi-final stage. On Tuesday, we have the first leg of Middlesbrough vs. Chelsea, with the winner sealing a spot at Wembley with the chance to win this year’s tournament. It’s certainly going to be a tough ask for Middlesbrough, who are sitting midtable in the Championship but they’ll be thankful to be at home and will hope to get some goals on the board to take to Stamford Bridge for the second leg.

Middlesbrough have had a poor season in the Championship. They came into the year looking for promotion, with the playoff spots being the minimum requirement, but they come into this 12th in the league. They have won three of their last five games and just signed Finn Azaz from Plymouth Argyle, but the season has been a disappointment on the whole. 

Chelsea, who are 10th in the league above, are also in the midtable of the Premier League. They’ve won three of their past four and it feels like they are turning a corner, although slower than some fans would like. It’s been a tough season for Mauricio Pochettino, who has not only had to bed himself in at a new club but also a whole host of signings. It’s hard to judge the job he’s done given the club’s huge injury list which has consistently robbed them of starting players all season long.

I’m expecting Chelsea’s slow and frustrating improvement to continue here.

In the Premier League this season, Chelsea have scored 34 and conceded 31 in 20 games. In terms of goals scored, they’re only a couple behind fourth-place Arsenal but they’ve allowed 50% more. Earlier in the season, Chelsea games were generally lower-scoring and more defensive but in the last couple of months, we’ve seen more scoring. In fact, since the start of December, we’ve seen both teams score in five of their seven games and they’ve then gone on to win three of those games.

We’ve also seen four of the last six Middlesbrough league games have BTTS land and against a team with Chelsea's firepower, even allowing for Nicolas Jackson and Christopher Nkunku to be missing, they are going to struggle to contain the scoring threat. In the Championship, Middlesbrough have a -1 goal difference, scoring 38 goals in 26 games this season and allowing one more.

Chelsea are simply too good to not win this game and they have the experience of high-pressure cup games, winning this competition two seasons ago. That said, I don’t trust them defensively and I think the Championship side will bag at least a goal at their home stadium..

My best bet: Chelsea to win & both teams to score (+190 at TonyBet)

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Middlesbrough vs Chelsea same-game parlay

Chelsea to win

Both teams to score — Yes

Cole Palmer anytime goal

+500 at bet365

First up, we’re backing Chelsea to win. They’re only midtable in the Premier League but they’re a far better team than Middlesbrough. Not only that, but after a tough start to the season, Chelsea have improved in recent weeks and come into this winning three of their last four.

One thing that has been an issue for Chelsea is that they’ve given up too many goals. In many ways, this is unlucky because they’ve had many defensive injuries that have caused continued rotation at the back. I don’t trust them to keep a clean sheet, and in front of a loud Riverside crowd, I think we’ll see Middlesbrough score a goal, although it won’t be enough to win.

To wrap up, we’re backing Cole Palmer to score. The young Englishman has been a huge success since arriving from Man City. He’s leading the club in league goals with eight and with Nicolas Jackson and Christopher Nkunku missing, it’ll put more pressure on Palmer to get the goals necessary for Chelsea. He should score here.

Learn how to bet a same-game parlay with these helpful tips and strategies.

Middlesbrough vs Chelsea side and Over/Under analysis

You can get Chelsea at -179 to win, which is slightly too short for me to consider betting and is why Chelsea plus both teams to score was my best bet. You can get +335 on the draw and +435 on a Middlesbrough win, but I wouldn’t back either of those. Chelsea are missing a lot of players, with injuries and internationals robbing them of great talent, but they still have more than enough to win this game.

The total goals market has Over 2.5 at -167 and Under 2.5 goals at +135. I think we’re going to see both teams score in this one and a total of three of four goals, so I’m backing Over 2.5 but I think you can just follow my best bet of Chelsea to win and BTTS and get far better value.

Middlesbrough vs Chelsea game info

Middlesbrough vs Chelsea key injuries

Middlesbrough: Darragh Lenihan CB (Out), Marcus Forss FWR (Out), Tommy Smith DEF (Out), Lewis O’Brien CM (Out), Paddy McNair CB (Out), Morgan Rogers CAM (Out), Sam Greenwood CAM (Out), Finn Azaz CAM (Out), Sam Silvera CAM (Out), Riley McGree FWR  (Out), Seny Dieng GK (Out).
Chelsea: Robert Sanchez GK (Out), Marc Cucurella LB (Out), Welsey Fofana CB (Out), Trevor Chalobah CB (Out), Reece James RB (Out), Romeo Lavia CM (Out), Nicolas Jackson STR (Out), Benoit Basiashile CB (Questionable), Ben Chilwell LB (Questionable), Christopher Nkunku FWR (Questionable), Carney Chukwuemka CM (Questionable).

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