In sharp contrast, the Sky Blues head into this fixture having lost each of their friendlies during July, heaping the pressure on Mark Robins's rapidly-changing squad.
On the back of winning the Championship title, Daniel Farke has taken the opportunity to freshen up his Norwich squad with youth and quality.
The Canaries have not faced the toughest of tests during pre-season, getting the better of Lincoln City and Huddersfield Town with three goals and two clean sheets to their name.
Nevertheless, Farke will be delighted with how his developing squad are blending together ahead of their Premier League opener against Liverpool.
While Norwich make the trip to Chesterfield in high spirits, Coventry are becoming increasingly desperate to find some positives from their friendly fixtures.
The Sky Blues have shipped 13 goals in defeats to Sevilla, MK Dons and Cheltenham Town, their only goal coming from Ricardo Dinanga during the first meeting with MK Dons.
Although Robins has not yet reached the stage where he will have long-lasting concerns, he knows that his side can ill-afford to start the new season in their current form.
Robins will be optimistic about a positive response when Coventry make their return to the Ricoh Arena to host Wolverhampton Wanderers on August 1.
However, full focus is currently on trying to cause a surprise against Norwich, opponents who sometimes struggled against them during the last campaign.
Gilmour may return to the Norwich squad having been left out of the encounter with Huddersfield.
Max Aarons could be provided with a start despite speculation regarding his future, and the same could apply to Todd Cantwell as Norwich wait for one of many interested clubs to meet their asking price.
Having played the full 90 minutes against the Terriers, new signing Pierre Lees-Melou could drop down to the substitutes' bench.
Josh Pask was an early withdrawal against Cheltenham, leaving him as an injury doubt for this contest.
Head To Head
As many as 124 competitive matches have taken place between these two sides, including three in the space of a couple of months at the turn of the year.
While Coventry held Norwich at Carrow Road in the Championship, they succumbed by 2-0 scorelines in the FA Cup and the reverse league fixture.
We say: Coventry City 0-2 Norwich City
Given their respective records in recent weeks, we can only predict a comfortable win for the Premier League side.
An improved performance may be Robins's priority, and keeping goals down to a minimum could be regarded as a successful outcome.