Boro have already secured a place in the playoffs but host a Sky Blues side who need a result on Teesside to ensure they will be joining Monday's opponents and Luton Town in the top six.
Match preview
Middlesbrough have found themselves in a unique situation over the past few weeks, with Michael Carrick's men knowing their top-four standing is safe with games to spare in the regular season.
Such security has led to changes in team selection from the Manchester United legend in recent times - perhaps a large reason why Boro have suffered back-to-back defeats recently.
A Hakeem Odoffin goal secured Rotherham United victory - and subsequent second-tier survival - against Carrick's charges last time out, with the visitors in South Yorkshire failing to dominant proceedings as they have become accustomed to this term.
Fresh off receiving the Championship's Player of the Year award, Chuba Akpom will be looking to sign off a remarkable regular season by reaching 30 league goals - the former Arsenal man needs a brace against Coventry to reach that significant milestone.
In a playoff race which has been widely contested, Middlesbrough arguably stand out as favourites heading into the playoffs next week, with the club's six-year association with the Championship possibly coming to an end.
Coventry are in the in-form side out of the playoff-chasing contingent, with the Sky Blues extending their unbeaten run to six matches with a comfortable 2-0 victory over West Midlands rivals Birmingham City last Saturday.
Josh Eccles opened the scoring in the third minute to send a sold-out Coventry Building Society Arena into hysterics, before a Jordan James handball gave Viktor Gyokeres the opportunity to net his 21st goal of the campaign from the spot - one which the Swede did not waste.
The realistic promotion push which Mark Robins's side are mounting this season feels greatly ahead of schedule - new owner Doug King has spoke about a five-year plan to get the club back into the Premier League - however with the nature of the Championship this year, Coventry may not get a better opportunity to get back onto the top table of English football.
The Sky Blues need just a point to secure a top-six finish this term, and if they managed to earn three points at Middlesbrough on Monday they would set up a semi-final clash with Boro starting next Sunday.
Having not tasted defeat on their last eight trips away from the CBS Arena, Coventry will be confident of securing a result on Teesside which could ultimately lead to their first Premier League berth since 2001.
Middlesbrough Championship form:
L
D
W
W
L
L
Coventry City Championship form:
D
D
W
D
W
W
Team News
Middlesbrough will be without Anfernee Dijksteel on Monday afternoon after the right-back was handed a straight red card during the loss at Rotherham last time out.
Paddy McNair, Tom Smith and Riley McGree returned to the matchday squad after their respective injuries during the Millers defeat - Carrick will be praying his side's medical room will empty out even more in time for the playoffs.
Aaron Ramsey was spotted earlier in the week back at his parent club Aston Villa as he recovers from an ankle injury suffered in the trashing of Norwich City - Boro are hopeful the attacker still has a part to play this season.
Coventry are confident of having talisman Gyokeres available for the trip to Teesside despite the Swede receiving a heavy kick in the win over Birmingham.
Ben Sheaf is set to return to the squad after a calf injury, although he is unlikely to be rushed into the XI with Robins having one eye on a possible run in the playoffs.
Middlesbrough possible starting lineup:
Steffen; Smith, McNair, Lenihan, Bola; Barlaser, Hackney; Jones, Akpom, McGree; Archer
Coventry City possible starting lineup:
Wilson; McNally, McFadzean, Doyle; Norton-Cuffy, Eccles, Kelly, Hamer, Bidwell; Gyokeres, Godden
We say: Middlesbrough 1-2 Coventry City
Middlesbrough are in an unusual situation heading into this game, and Carrick may opt to field a second-string side in order to give his star men a rest ahead of the start of the playoffs next week.