Middlesbrough vs Milwall: Big Bet Preview

Credit: Cristi Dangeorge

Middlesbrough vs Millwall
(Fri 3 Apr, 12:30pm UK - Sky Sports)

The Championship automatic promotion race looked all-but done a few weeks ago, but it’s suddenly burst into life! Coventry are running away with the league, leaving second place to be scrapped over by the three sides still in contention. They’ve all faltered and dropped points in recent weeks as the weight of late-season pressure begins to take it’s toll, who will end up top of the pile as the final month of the season looms? Fourth-placed Millwall make the long trip up north this weekend to face Boro in second, knowing a win would fire them above their hosts and give them the advantage going into the final six games. For the Teesside outfit, three much-needed points would get their promotion charge back on track after a run of less-than-ideal results has left the door open for them to be overtaken despite looking the clear favourite to go up alongside the Sky Blues just a few short weeks ago. Which of these sides will make Good Friday a great one? One thing’s for certain, those affiliated with Ipswich town will be keeping a close eye on this one. Championship promotion, it’s as big as it gets in this week’s Tipple Big Bet!

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This weekend’s game will be crucial in the context of the battle for automatic promotion into the promised land. As much as we all prefer the Football League, the riches and allure of the Premier League are undeniable and these clubs will be going all-out in this game to get themselves over the line.

For Middlesbrough, promotion would end a nine-year stint in the second tier following relegation in 2017. Should the visitors finish up in second place, it would be a first-ever Premier League appearance for the club, and mark their return to the top tier of English football for the first time since their brief stint in the division from 1988-90.

Ipswich are waiting in the wings for either of these to slip up, if they win their game in hand they can take the advantage in the race for second, but they’ve also shown they’re prone to a slip-up against a weaker side when they fancy it.

Here are the standings going into this Easter weekend for reference:

1st: Coventry, 39 PL, +41 GD, 80 Pts

2nd: Middlesbrough, 39 PL, +22 GD, 71 Pts

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3rd: Ipswich, 38 PL, +28 GD, 69 Pts

4th: Millwall, 39 PL, +9 GD, 69 Pts

These two rejoined the Championship from the Premier League and League One respectively in the same summer. While Boro have struggled to regroup and take that final step to become a promotion-winning team once again, Millwall have stuck to their business model of selling their in-demand players and rebuilding from the ground up to finally challenge for promotion. With everything on the line, who will emerge victorious and go into the run-in with the advantage in this week’s Big Bet?

Form

Boro were on a 5-game winning streak going into their top of the table clash against Coventry in mid February, and looked to be cruising to automatic promotion, and maybe even the title. Since losing that game and dropping from top back to second, their standards have slipped and the race for automatic promotion has been blown wide open. They’ve actually only lost once in the 7 games proceeding the loss to Coventry, but 4 of those have ended as disappointing draws to inferior opponents. Relegation threatened Oxford, Leicester, and Blackburn all escaped clashes with Middlesbrough with a point, as did mid-table Bristol City, and Charlton managed to snatch all 3 points from their trip to the Riverside. They still managed impressive victories away at Birmingham and QPR in the midst of this run, but Kim Hellberg’s side now sit just 2 points clear of the chasing pack after 3 games without a win. 

Millwall have also dropped a few points in recent weeks, but have proven that they’re able to turn it on when it matters in the big games. They’ve won 6, drawn 2 and lost 2 in their last 10 outings, with huge wins against play-off chasing Wrexham, Derby, and Hull across that period as well a spirited draw away at Ipswich in their most recent fixture. Their issue seems to be the on-paper “easier” games, with their recent losses coming in home fixtures against struggling Pompey and Blackburn.

Millwall haven’t won for 2 games, but they love a big fixture. Can Boro rise to their visitors’ level and end their 3 game winless run?

Head-to-head

These two met in the second game of the season, Boro running out emphatic 3-0 winners at The Den. Things have changed since then - namely the Middlesbrough manager - and you’d expect this time around to be much more evenly matched.

Their last 10 meetings have ended up in 4 wins for Middlesbrough, 4 Millwall wins and just two draws. There’s very little to split the two in their recent history, could Boro do the double over a close promotion rival? Or will Millwall exact their revenge for the early-season humiliation?

Key Battle

Matt Targett vs Femi Azeez

It feels like we’re witnessing a true breakout season from Femi Azeez this year in his second season at Millwall after joining the London club from Reading in the summer of 2024. He managed 2 league goals and 5 assists last term, not bad for a debut year at this level. This season, however, he’s found a different level.

He already has 8 goals and 7 assists to his name, and is showing no signs of slowing. Azeez has proven he can score with either foot and with his head if necessary, preferring to cut inside onto his left foot from his position out wide on the right. Goalscoring isn’t his only strength either, he is in the 97th percentile for big chances created per 90 amongst his fellow wingers, and 99th for successful crosses. Let him cut onto his left foot, and he’ll bend it into the top corner. Force him out wide onto his right, he’ll whip in a cross for a teammate to tap home. Azeez has really come into his own this season as one of the Championship’s premier attacking talents. If he doesn’t go up with Millwall, I wouldn’t be surprised to see one of the promoted teams fork out a sizeable chunk of change to bring Azeez with them to the Premier League.

Tasked with marshalling him this time around is experienced full-back Matt Targett. Targett is no stranger to contributing to the attack either, netting 4 goals and providing 3 assists from defence this year, including a notable brace in a huge win away at Birmingham. His experience and guile could be exactly what Boro need to try and lock down a live-wire like Azeez, and his creative prowess is notable enough that Azeez will have to think twice before allowing Targett too much room down the flank. Capable defensively and enough of a threat going forward to make Azeez stop and think, is Matt Targett the answer to the question of how to stop one of the leagues most dangerous forwards?

Preview

With so few games left in the calendar, they’re all big. But this one just means more. With just 2 points separating these sides and only 7 games to cement their place, everyone inside the Riverside will be on edge.

With these two storied clubs facing off with promotion potentially on the line, can Boro arrest their slide and continue on a path to promotion? Or will Millwall leapfrog the Teesside outfit into the automatic places?

Whatever happens, with Ipswich not playing until Monday, the Tractor Boys will have a keen eye on this one.

Tipple Difficulty Rating: 9.5/10