Coventry boss Chris Coleman was forced to name five teenagers in his starting XI as a number of first-team players were away on international duty and one of them, Ashley Cain, created the first chance of the night in the ninth minute.
Cain was played in down the right wing and delivered an excellent cross to the near post where Freddy Eastwood got in front of his defender to flick a header wide.
The rest of the half petered out with the air of a testimonial while Eastwood did his best to rouse some form of atmosphere after the break with another header which sailed narrowly wide.
Hartlepool boss Chris Turner introduced substitutes Boyd, James Brown and Colin Larkin in a bid to provide some inspiration for the hardy handful of fans who had made the 185-mile trip and Brown almost broke the deadlock with quarter of an hour left.
Denis Behan flicked the ball on but Brown's attempted lob was well saved by former Hartlepool goalkeeper Dimi Konstantopoulos to ensure the 6,055 fans present would have to endure another 30 minutes of extra time.
Hartlepool left-back Peter Hartley then forced Konstantopoulos into a decent save with a speculative 30-yarder before Anthony Sweeney headed wide as the visitors had their best spell of the match.
And Boyd finally broke the deadlock in the 105th minute when he controlled Larkin's cross from the right on his chest and shot powerfully under the body of Konstantopoulos from 10 yards out.
Cain, Adam Walker and Callum Wilson all had chances to force an equaliser for the home side in the dying moments but Hartlepool hung on for a deserved win and a crack at the Clarets.