These two teams, who finished fifth and fourth respectively in the table, are no strangers to each other having met in their final league fixture earlier in the week.
Match preview
Whether it has been issues with their pitch, stadium or ownership, things have not been plain-sailing for Coventry this season, the Sky Blues also spending the first couple of months in the relegation zone.
However, Mark Robins has still been able to produce one of the most unlikeliest promotion bids for some time, Coventry losing just one of their final 17 league games to earn fifth spot.
Three wins from four fixtures left Coventry needing a point from their contest at Middlesbrough on Monday, both clubs aware of the significance of the game given a possible playoff reunion.
Coventry initially led before being pegged back ahead of half time, and Robins's side then showed their character as they earned a share of the spoils at the Riverside Stadium.
Whether the result and performance will have any relevance on the upcoming two-legged tie, only time will tell, but avoiding defeat at a ground where Middlesbrough have generally dominated under Michael Carrick cannot be a bad thing.
Since it became clear that Boro would not finish in the automatic promotion places and a top-four position was all but guaranteed, their results have dropped off.
That is partly down to Carrick having to deal with injuries, but two wins from eight matches is hardly ideal form heading into this stage of the season.
Like Coventry, Middlesbrough spent time in the relegation zone during the early weeks of the season, Carrick instigating a remarkable upturn in results in his first permanent managerial role.
Nevertheless, for all the goals that Boro score on a regular basis, they have kept only one clean sheet in 11 outings and have just the joint-11th best defensive record in the Championship since Carrick's arrival.
Coventry City Championship form:
D
W
D
W
W
D
Middlesbrough Championship form:
D
W
W
L
L
D
Team News
Having made just one substitution during the showdown between these two sides earlier in the week, Robins is likely to stick with the same Coventry XI.
Kasey Palmer, Callum O'Hare and Fabio Tavares are all expected to remain on the sidelines for both legs of this last-four clash.
Meanwhile, Carrick has already revealed that he does not expect any of his injured Boro players to come back into contention.
That would see Dael Fry, Jonny Howson, Aaron Ramsey and Marcus Forss all stay on the sidelines for the time being, and it is plausible that Carrick names the same starting lineup from Monday.
If alterations are made, Dan Barlaser and Matt Crooks are both pushing for chances in central midfield and in the final third respectively.
Coventry City possible starting lineup:
Wilson; McNally, McFadzean, Doyle; Norton-Cuffy, Hamer, Kelly, Eccles, Bidwell; Gyokeres, Godden
Middlesbrough possible starting lineup:
Steffen; Smith, McNair, Lenihan, Giles; Hackney, Mowatt; Jones, Akpom, McGree; Archer
We say: Coventry City 1-2 Middlesbrough
With Coventry having the greater momentum during the run-in and from Monday afternoon, they will fancy their chances of earning a first-leg win. However, we feel that Boro will click back into gear, their talented attack giving their team the edge ahead of the second leg.