Chelsea vs Middlesbrough prediction, odds, expert football betting tips and best bets for Carabao Cup semifinal

Chelsea hope to turn around a disappointing deficit in their Carabao Cup semifinal against Middlesbrough as they return home for the second leg on Tuesday.

While the Blues have looked better in recent weeks as Mauricio Pochettino begins to assert his influence over one of the Premier League’s youngest squads, the first leg saw the Blues revert back to their old ways, missing countless chances and committing mental lapses at the back.

A 37th minute goal by 21-year-old Hayden Hackney was enough to see Middlesbrough through to victory which they will now be tasked with maintaining in a much more hostile environment.

With Christopher Nkunku again out injured along with nine other first-team players, the Blues have been forced to dip deeper and deeper into their squad of young, inexperienced players who will shoulder the weight of pushing for a comeback and a place in the late February final at Wembley.

USA: Click here to see the latest odds for Chelsea vs Middlesbrough and bet Carabao Cup matches

Chelsea vs Middlesbrough prediction, odds

  • Moneyline lean: Draw (+550 on DraftKings)
  • Score prediction: Chelsea 1-1 Middlesbrough
  • To advance: Middlesbrough (+220 on DraftKings)

The Blues are the better side on paper, and they pummeled Middlesbrough in the first leg, so there should be chances for them to at least find a goal. Yet they could struggle to find enough to really take hold of the aggregate scoreline, and Middlesbrough will know just one goal of their own could be enough to push them through to Wembley.

This Chelsea side has talent, and they should improve if they give Mauricio Pochettino time to develop the squad, and time to get the flurry of injured players fit. Yet as of now, they struggle to deal with adversity, and if Boro deliver a punch, it’s hard to see the Blues getting back up for a response.

While the moneyline may not be the best play here, because it’s feasible to think Chelsea can do enough to find a one-goal winner to at least send the tie to extra-time. Instead, Middlesbrough to advance is a great play at solid plus odds, as you would back them to win a penalty shootout with the pressure mounting.

Chelsea win -370
Draw +550
Middlesbrough win +900
Both teams
to score Y/N
-115 / -110
Over / Under
3.5 goals
+110 / -150
to advance
to advance

Chelsea vs Middlesbrough match facts

  • Date: Tuesday, Jan. 23, 2024
  • Kickoff time: 8 p.m. local (3 p.m. ET / 12 p.m. PT)
  • Location: Stamford Bridge (London, England)
  • Referee: John Brooks, VAR: None*
  • Last meeting: Middlesbrough 1-0 Chelsea (Jan. 9, 2024 | EFL Cup)

* Because VAR was not available at Middlesbrough’s home venue Riverside Stadium, the EFL decided that VAR would not be used across either Carabao Cup semifinal matchup this year.

Chelsea vs Middlesbrough best bet

  • Pick: Under 3 total goals
  • Odds: +110 (DraftKings)

At this stage of the season, while Chelsea have proven they can create chances in bunches, it’s too difficult to trust them to finish those opportunities off. The Blues have been putrid in front of goal all year long, and while it appeared to be turning a corner, they have recently reverted back to their old habits.

With Nicolas Jackson on international duty and Christopher Nkunku yet again out injured as he has been all year, Cole Palmer has been forced into a false nine role, which weakens the attack on the whole.

Jackson has been one of the worst finishers in England this year, but even in his absence, the rest of the side hasn’t managed to pick up the slack. In the first leg, they whalloped Middlesbrough for 18 shots worth 2.6 expected goals, yet came up completely empty with Palmer, Conor Gallagher, Noni Madueke, and Mykhailo Mudryk all missing opportunities. Even at home, Middlesbrough should manage to keep a lid on the game if Thomas Glover can repeat his first leg performance.

Chelsea vs Middlesbrough prop bet

  • Pick: Goal scored in kickoff to 15th min interval — YES
  • Odds: +175 (DraftKings)
  • Pick: Goal scored in 16th to 30th min interval — YES
  • Odds: +140 (DraftKings)

Both teams will know that every goal is crucial to the end result of this two-legged matchup, and the opening half-hour of that will be vital. While we don’t expect this to be a high-scoring affair, it remains sensible that both teams — Chelsea especially — will know the first goal could ultimately decide the course of the match.

With the Blues sure to push for an early goal to give them ample time to find an aggregate winner and avoid extra-time, Middlesbrough will also know a second goal could put them out of sight. Thus, the first half should be much  more entertaining than the second half, which could be cagey as Boro shut down and hold onto either a lead or level scoreline, should it remain intact.

In low-scoring matches, it’s hard to predict which half will emerge as higher scoring, as one goal could throw off the balance, but backing a goal in the first half-hour is reasonable, and with a one unit play on both selections separately, even just one cashing would return a profit.

Chelsea vs Middlesbrough live stream, TV channel

  TV channel Streaming
Canada  — DAZN Canada
UK Sky Sports Football, Sky Sports Main Event Sky Go

The U.S. broadcast rights for the 2023/24 Carabao Cup are owned by ESPN, who has placed the entirety of the competition on its premium streaming service ESPN+.

In Canada, the competition is streamed by DAZN, while this match will be available in the UK via Sky Sports.


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