Boro were the highest scorers in the Championship after Michael Carrick arrived, and the Teesiders are the favourites to earn the third promotion spot.
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Middlesbrough have been exiled from the Premier League since 2017, but they have an excellent chance to end that absence.
Standing in their way from a spot at Wembley later this month are Coventry.
Mark Robins' side were down in 20th in December but only lost one of their last 16 games to finish fifth.
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The Sky Blues were in League Two as recently as 2018, and they haven't been in the top-flight since 2001, so this is a massive chance for them.
Coventry vs Middlesbrough: talkSPORT coverage
This Championship play-off semi-final first leg will take place on Sunday, May 14.
Kick-off at the Coventry Building Society Arena is scheduled for midday.
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talkSPORT will have live coverage from the West Midlands, with Adrian Durham serving as your host.
Commentary will then come from Ian Danter and former Scotland striker Chris Iwelumo.
talkSPORT.com will have the best of the reaction from Coventry.
To tune in to talkSPORT or talkSPORT 2 through the website, click HERE for the live stream.
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You can also listen via the talkSPORT app, on DAB digital radio, through your smart speaker and on 1089 or 1053 AM.
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Coventry vs Middlesbrough: Team news
The hosts will likely be without Ben Sheaf as he continues recovering from a calf tear.
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However, he was an unused substitute in the last game of the season and has an outside chance of being involved but the return leg appears to be a more realistic date.
Meanwhile, the visitors are set to be without a number of key players.
Jonny Howson, Dael Fry, Aaron Ramsey and Marcus Forss are still on the sidelines and are unlikely to play any part here.
But Ryan Giles and Riley McGree are fully fit, while Darnell Fisher made his first appearance in two years in the 1-1 draw with Coventry earlier this month.
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Coventry vs Middlesbrough: What has been said?
Coventry boss Robins wants his side to carry on their momentum.
He said: "It's brilliant to be in the play-off mix, and I don't think many people would have given us a chance of doing that earlier on in the season because the fact is we have had so many obstacles thrown in our way.
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"But everyone has overcome those and to get into the play-offs is fully deserved.
"I think we have played some really good football along the way. Yes, we'll embrace it, and yes, we'll give it everything we have got, absolutely we will.
"There's a lot of other clubs who thought they were there and had been higher and they're not, and that's the reality, and we want to seize every opportunity that we possibly can do.
"We are looking forward to it. There's absolutely nothing to lose and we're going into the game with momentum and confidence that's built from that momentum.
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"We know we're facing a really good team, as we saw when we faced them last week, so we have to embrace this opportunity."
Coventry vs Middlesbrough: Match facts
Coventry have won four of their last five home games against Middlesbrough (L1), all in the Championship, with the Sky Blues winning 1-0 this season with a goal from Viktor Gyökeres.
The away team has won just one of the last 16 meetings between Coventry and Middlesbrough in all competitions, a 2-1 win for Middlesbrough in March 2021 when they were managed by Neil Warnock.
This is Middlesbrough's fifth Football League play-off campaign, with all of their previous four coming at this level. After winning promotion in their first in 1987-88, they haven't won promotion via this method on any of the other three occasions, in 1990-91, 2014-15 and 2017-18.
Coventry City have only featured in the Football League play-offs on one previous occasion, winning the 2017-18 League Two play-offs via eliminating Notts County in the semi-final and Exeter City in the final at Wembley.
The team finishing fourth in the Championship has won promotion via the play-offs in four of the last nine seasons, including two of the last three (Fulham in 2019-20, Nottingham Forest in 2021-22).
Middlesbrough scored 84 league goals this season, their most in a season since 1966-67 (87 in the third tier). 65 of those goals have been scored since Michael Carrick's first game in October, eight more than any other side has scored in the Championship since then.
Coventry's Viktor Gyökeres was involved in more goals than any other Championship player this season (21 goals, 10 assists). He also ranks in the top-five for shots attempted (137, 2nd), shots on target (58, 2nd), chances created (85, 5th) and touches in the opposition box (350, 1st). His 350 touches in the opposition box is the second-most on record (since 2013-14) by a player in a regular Championship season, behind only Callum Wilson in 2014-15 (385).
Since his first start for Middlesbrough in January, no player has been involved in more Championship goals than Cameron Archer (17 - 11 goals and 6 assists - level with Viktor Gyökeres). Archer's 11 goals have come from just 16 shots on target, scoring with 69% of his on-target attempts for the club.
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