Having each lost in the playoffs in 2022-23, these two teams begun their campaign with defeats to Leicester City and Millwall respectively.
Match preview
While Mark Robins would have recognised that his side had the toughest start to the season possible, he would have been optimistic about getting at least a point on the board at Leicester City last weekend.
However, despite doing more than enough to earn at least a share of the spoils, the 2022-23 Championship playoff runners-up conceded two late goals to lose by a 2-1 scoreline.
Performance-wise, Robins could have only been left encouraged, but three days on from that setback, Coventry succumbed to a 2-1 defeat at the hands of AFC Wimbledon in the EFL Cup.
As at the King Power Stadium, the Midlands outfit shipped two goals during the closing stages to suffer defeat from the jaws of victory, and Robins has a job on his hands to lift his team for this fixture.
These clubs are no strangers to each other having met in the playoff semi-finals in May, Coventry coming through by a 1-0 aggregate scoreline after edging the away second leg.
Middlesbrough will have adopted a similar mentality to Coventry ahead of this campaign, taking the positives from what was a surprise bid for promotion.
Nevertheless, Michael Carrick watched his team lose out 1-0 at home to Millwall in their second-tier opener, lowering the mood at the Riverside Stadium.
Although Boro responded by overcoming Huddersfield Town in the EFL Cup on Tuesday, they could only prevail 3-2 despite their hosts being down to 10 men from the 13th minute.
Having made alterations for that fixture, Carrick will hope that some of his new arrivals are now acclimatising themselves to this level of football, yet the North-East outfit are clear underdogs in this fixture given that Coventry performed promisingly enough at the Foxes.
Coventry City Championship form:
Coventry City form (all competitions):
Middlesbrough Championship form:
Middlesbrough form (all competitions):
Team News
With this being the third game for Coventry in the space of a week, Robins opted to make seven changes to his side for the match at AFC Wimbledon.
Barring any fitness issues, those same seven players should slot back into the side, with recent big-money addition Haji Wright among those who may drop down to the substitutes' bench.
The trio of Jamie Allen, Callum O'Hare and Fabio Tavares all remain sidelined through injury.
Isaiah Jones and Samuel Silvera both came into the Boro XI for the Huddersfield fixture in midweek and got their names on the scoresheet.
However, Carrick is expected to drop the two wingers back down to the bench, and could name the same side that lost at Millwall with Chuba Akpom still out injured and being linked with a move elsewhere.
Coventry City possible starting lineup:
Wilson; Thomas, McFadzean, Latibeaudiere; Eccles, Hamer, Sheaf, Dasilva; Palmer; Godden, Simms
Middlesbrough possible starting lineup:
Dieng; McNair, Fry, Lenihan, Coulson; Barlaser, Hackney; Forss, Crooks, McGree; Rogers
We say: Coventry City 2-1 Middlesbrough
Based on their results over the last week, this is a difficult match to predict. Middlesbrough will be buoyed by seeing off Huddersfield in the EFL Cup, yet we feel that Coventry have done everything but win, leading us to predict a narrow home victory.