Chelsea vs Middlesbrough Predictions and Picks: Desperation Kicks In

Following a disappointing first leg where Chelsea somehow failed to score despite many chances, they need a big game vs. Middlesbrough to advance. With so many injuries and other absences, Chelsea might be in trouble despite being big favorites.

Jason Ence - Contributor at Covers.com
Jason Ence • Betting Analyst
Jan 20, 2024 • 10:48 ET • 4 min read
Cole Palmer Chelsea EFL
Photo By - USA TODAY Sports

The second leg of the EFL Cup semi-final will see Chelsea and Middlesbrough battling for a place in the final. Our soccer betting odds have the Blues as overwhelming favorites to win in regulation.

With three upcoming matches over nine days, Mauricio Pochettino will be happy to have had 10 days off since their last match. But that’s not enough to get any of his injured players back, with nearly a full squad either on the trainer’s table or away for international duty. Still, he has the quality at his disposal to overcome a 1-0 deficit from the first leg and reach the final.

Middlesbrough will hope to somehow do enough to make that advantage count. They were fortunate to escape with the win in the first leg after conceding 18 shots at home, ending a nine-match losing streak against the Blues. Now they must travel to Stamford Bridge, where manager Michael Carrick’s side hasn’t won in their last 24 visits.

Our Chelsea vs. Middlesbrough picks and predictions for the EFL Cup semi-final on Tuesday, January 23 explain why neither side is likely to walk away unscathed, and how that benefits you as a bettor.

Chelsea vs Middlesbrough best odds

Brighton & Hove Albion Chelsea Manchester United Middlesbrough
-455 Moneyline +1,000
+600 Draw +600
Over 2.5 (-250) Total Under 2.5 (+187)

Odds courtesy of bet365 on January 23, 2024.

Chelsea vs Middlesbrough picks and predictions

It’s not just that Chelsea are missing players, but where they're missed. Not a single area of the pitch has been spared, but their defense has been hit hardest of all.

Goalkeeper Robert Sanchez is injured, as are defenders Reece James, Wesley Fofana, and Marc Cucurella. Trevoh Chalobah is also a doubt for the match.

While they did see Ben Chilwell return with a cameo appearance in their win over Fulham, he’s still probably not at a place where he can start. The trade-off in that fixture was the loss of Malo Gusto, who was forced off in stoppage time with an injury.

That’s led to Chelsea having to field a side riddled with inexperience, plus a lack of familiarity at the back. Middlesbrough took advantage of that in the first leg, as they failed to pick up the run of Hayden Hackney. Isaiah Jones was able to pick him out between four Blues after a long ball into the final third, for the only goal of the match.

But Middlesbrough nearly scored in the opening minute. Emmanuel Lath had a good chance inside 60 seconds but hit it right at the keeper, signifying the side’s intent. They managed six shots on the day, including three from inside the penalty area, and should’ve done better with an opportunity just three minutes after halftime.

Speaking of doing better, Chelsea will still be wondering how they failed to score a goal. Despite having an xG of 2.60 for the match, the Blues failed to find the back of the net with any of their 18 shots on the day. Their wasteful finishing was punished, as they put just five efforts on goal and came up empty despite three big chances.

Pochettino may tinker a bit with the front line, where he has midfielder Cole Palmer playing as a makeshift striker in the absence of Nicolas Jackson and Christopher Nkunku. Either way, he has more than enough weapons to find at least one goal today, if not more.

And if the Blues want to advance, they will need more than one goal. That’s because I fully expect Middlesbrough to once again breach the Chelsea defense. They’ve had a solid campaign on the road, having been shut out just twice in 19 away fixtures in all competitions.

Chelsea have managed three clean sheets in their last five matches at Stamford Bridge, but I don’t see that happening again today. Middlesbrough are third in the EFL Championship in shots on target this season, and only Plymouth Argyle puts a higher percentage of efforts on target.

They only hold the eighth-most possession per match of any team in the league, and they were happy to cede 72% possession to Chelsea in the first leg. And despite that, they still put nearly half as many shots on goal as the Blues from six efforts.

So we’re backing both teams to find the back of the net, which TonyBet is offering at -118 odds. Then sit back and enjoy what should be an entertaining fixture.

My best bet: Both teams to score — Yes (-118 at TonyBet)

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Chelsea vs Middlesbrough same-game parlay

Both teams to score - Yes

Cole Palmer to score or assist

Cole Palmer 3+ shots

Palmer has been at the heart of Chelsea’s attack of late, and we’re backing him to be involved yet again for our same-game parlay.

He's scored three goals and assisted two others over his last six matches across all competitions, registering 12 key passes in that time. He scored the only goal in their victory over Fulham last time out, as he converted from the penalty spot in first-half stoppage time.

With him on penalty duty and likely leading the front line, I’m backing him to once again either score or set up a teammate. Palmer registered six touches in the Middlesbrough penalty area in the first leg, the second-most of any player. He had 1.45 xG on the day from four shots.

Palmer has attempted at least three shots in five of his last seven matches, including four matches with four or more. We’ll back him to get at least three attempts off at the Bridge.

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

Chelsea vs Middlesbrough side and Over/Under analysis

To say the Blues are favored to win in regulation is an understatement. Their odds on the 3-way line range between -400 and -550, with the away side getting +1,000 to pull off a second straight upset. The draw also pays handsomely, with +600 on offer.

Unlike most knockout fixtures, the EFL Cup typically goes straight to penalties if tied — but that stops in the semi-finals. If Chelsea are ahead by a single goal, the match would see an extra 30 minutes played. Chelsea need to win by two or more to advance after regulation, while a draw or loss would send Middlesbrough through.

Pochettino will want to avoid that with an FA Cup fixture coming up in three days, so expect the Blues to be on the front foot from the opening whistle. They don’t need to do anything differently from the first leg, aside from actually converting their chances.

The Blues have won six straight and are eight unbeaten on the trot at home, and they should have enough to get a multiple-goal win but extra time could be on the cards. One thing to watch out for is the wind. With gusts of up to 40 mph expected, there could be some unexpected opportunities against Chelsea’s back line on the counter-attack.

The total is also quite juiced for those expecting to play the Over 2.5 line. The best number on offer is -240, with most books having already shifted to the 3.5 total instead. The Under there is -130 or more, with plus-odds for Over 3.5 goals.

I fully expect there to be three or more goals, but Chelsea’s finishing issues could derail that, which is why I opted against including it in my best bet as a combo play. While they’ve seen more goals at home this season, Chelsea have been held to a single goal in two of their last four at the Bridge.

Overall, the Blues have managed just one goal in their last two fixtures, despite taking a combined 32 shots in those matches. That said, the rest period should help with fatigue, and with Middlesbrough finding a goal at some point, the Over 2.5 is a decent parlay piece. But I’m staying away from the elevated 3.5 line with how Chelsea’s been finishing.

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Chelsea vs Middlesbrough game info

Location: Stamford Bridge, London, UK
Date: Tuesday, January 23, 2024
Time: 3:00 p.m. ET
TV: ESPN+
Weather: 56F, 48F wind chill, 3% POP, 21-41 mph wind, 84% humidity

Chelsea vs Middlesbrough key injuries

Chelsea: Nicolas Jackson F (Out), Reece James D (Out), Christopher Nkunku F (Out).
Middlesbrough: Emmanuel Lath F (Out), Seny Dieng GK (Out), Isaiah Jones M (Doubtful).

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Jason Ence - Covers
Betting Analyst

Jason has been hooked on soccer since watching Real Madrid and Manchester United in the 2003 Champions League, and has been betting on the sport for nearly 15 years. He has given soccer gambling and fantasy advice for nearly a decade, writing for sites including Rotowire, SB Nation, and The TwinSpires Edge.

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