Six of his players were injured last night and two others were committed to international matches.
In deciding how to manage those absentees while obeying competition rules preventing token line-ups, Grayson pieced together the strongest team he could justify while topping up his bench with an untested striker in Davide Somma and a junior goalkeeper in Ryan Jones. The approach paid off but only just.
Among the small but respectable crowd at Elland Road, Jones would have been familiar only to those who followed United's reserve squad closely last season.
United's losses were so severe that even Frank Fielding - signed on loan from Blackburn Rovers specifically to compensate for an injury to Shane Higgs - was stationed elsewhere with England's U-21s, leaving Jones to deputise for Casper Ankergren. It was, to that degree, a case of muddling through.
With every professional available to him, the demands of the Johnstone's Paint Trophy would not have bothered Grayson, but a second-round tie against Darlington in a competition of low priority was not a game his squad needed.
Were it not for the postponement of Saturday's league game at Bristol Rovers, United would have been cursing it. Satisfactory, then, was the win delivered by his carefully-constructed team; less so the performance or the loss of another player - Somma - to yet another injury.
United imposed themselves on Darlington with two goals claimed inside half-an-hour, scored by players who have seen little or no football this season and should feel happier this morning for the chance of acknowledgement. Not all of their team-mates will be so content.
Andy Robinson registered Leeds' first goal and Tresor Kandol their second, a source of confidence for United's winger and a red letter day for the club's striker.
On the last occasion that Kandol scored in a first-team match at Elland Road, Leeds were days away from the 2008 play-off final. It has been that long.
His contribution over 45 minutes may convince Grayson that Kandol is worth more than simply a squad number, particularly while Luciano Becchio deals with an injured ankle. Robinson too enjoyed the type of lively first half he probably needed. To that end, the fixture had its uses, though Grayson made no effort to disguise how angry he was with his team's failure to kill the tie.
Despite the Trophy's meagre profile, its regulations dictated that he field six of the 11 players with most club appearances on their records this season, a requirement that Grayson was able to meet despite making six alterations to the team that drew with Charlton Athletic on Saturday.
Anxious though he was to avoid incurring a fine, Grayson's options were not exactly vast. They did, however, include Kandol, a player who has been virtually anonymous at Elland Road for the past year and a half. Promoted to the starting line-up - an announcement that drew applause from the crowd - his rare inclusion spoke of the lengths his manager had gone to in fulfilling last night's match.
Perspective was still necessary against a club with more endemic problems.
Darlington came to Elland Road as the Football League's lowest-ranked team and one who, until this morning, were technically without a manager.
Steve Staunton, Leeds' former assistant, was appointed on Monday with the intention of taking charge today, and while he attended last night's game, he declined the chance to watch his squad from the touchline, preferring to take a seat in the directors' box.
Ken Bates, the man who ordained that Staunton should take his leave of Elland Road 10 months ago, was not there to greet him.
From that vantage point, Staunton's early viewing was not particularly pleasant.
Darlington made the effort to be expansive and use possession carefully but their defence was only ever one clean strike away from being breached.
Nick Liversedge, their goalkeeper, dealt with one firm header from Kandol by touching it over Darlington's goal and did so again with more urgency when a second header from the striker dropped beneath his crossbar.
Those two efforts materialised inside 15 minutes; by the 20th, Robinson and Aidan White were pulling shots wide from positions where Liversedge would have anticipated having a save to make. No surprise, then, that the damn should burst four minutes later.
A foul on White gave Robinson his first chance to attack Liversedge with a free-kick and his low set-piece crept inside the keeper's near post, carried over the line by a very minor deflection. It should, even then, have been the beginning of a ruthless end.
In the 28th minute, Neil Kilkenny fed Kandol from the halfway line and the forward's screaming shot from the edge of the box ripped into the roof of Darlington's net.
It gave Staunton much to ponder as he prepared to sit down behind his new desk. In Darlington's favour will be their reaction to United's goals and their improvement in the second half.
Caretakers Craig Liddle and Neil Maddison immediately removed defender Matthew Plummer to make space for substitute and forward Mark Convery, and the change brought a goal in the last minute of the first half.
Jamie Devitt, who had earlier curled a wild shot over the bar after Gary Smith cut open the left side of Grayson's team, picked out Convery with a cross which Ankergren failed to reach and Convery side-footed into an empty net.
Darlington's sixth goal of the season did not flatter United's defence.
Kandol was substituted at half-time after illness overcame him, and Enoch Showunmi appeared in his place, a meaningful comparison between fringe strikers with similar attributes.
Forty-five stagnant minutes followed, however, and Convery was inches from equalising at Ankergren's back post with an hour gone. Grayson - aware of the decreasing intensity - was vocal in demanding better from his technical area.
He gave Somma his debut as the game wore on but the contest was petering out, save only for Kevin Gall's shot at one end and a low strike from Showunmi at the other, parried with one hand by Liversedge.
Liversedge's night would later end with a red card, shown to him in injury-time for a professional foul on Showunmi. The unnecessary dismissal came so late that midfielder Jeff Smith, improvising as a keeper, had only one wayward free-kick from Robinson to worry about.
Four minutes before the sending off, United's bewildered staff looked on as Somma collapsed without a player near him and was helped from the pitch, leaving Leeds with no remaining substitutions and 10 players. Somma had appeared from the bench no more than 15 minutes earlier; Grayson could not make it up.
YEP chief football writer Phil Hay rates how Leeds United's players performed against Darlington last night.
Casper Ankergren: His handling on a wet surface was pretty reliable during the game but he seemed to misjudge Devitt's cross when Darlington scored, leaving an open goal behind him...5
Leigh Bromby: Not a great night for Bromby who was hassled incessantly by the visitors and failed to impose himself at right-back. Caught out of position too often...5
Lubomir Michalik: Looks increasingly confident and - step by step - is returning to something like his best form. The pick of the defenders last night and almost scored twice...7
Richard Naylor: His display might have been overlooked amid United's mediocrity, but he won challenge after challenge in the second half and is one player who can hold his head up...6
Andrew Hughes: Did what he always does and kept the door closed down the left flank. Nothing spectacular in Hughes' display but Darlington were never going to score from his side of the pitch...6
Andy Robinson: Enjoyed a very encouraging first half-hour in which he toyed with Darlington and scored the opening goal but the tempo of his display subsided sharply...5
David Prutton: Last night was a chance for Prutton to catch Grayson's eye and one the midfielder failed to take. A frustrating evening when nothing came off and passes went astray...4
Neil Kilkenny: His through ball to set up Kandol's goal was Kilkenny at his best, and there were flashes of the Australian's invention throughout the game. Not as dominant as he can be...6
Aidan White: Used as a left winger, a role he is quick enough and skilful enough to fill, and although White was quiet in parts of the game, his more direct runs gave Darlington trouble...6
Tresor Kandol: It is easy to forget that Kandol is still on United's books, but his goal was superb and he caused no end of problems. A strong claim for more involvement under Grayson...7
Mike Grella: Hobbled off on 70 minutes after a hard, unrewarding shift. Darlington kept a tight leash on him throughout the game and his tireless running did not amount to much in return...5
Substitutes: Enoch Showunmi (for Kandol, 46)...5
Davide Somma (for Grella, 70)...5
Bradley Johnson (for Hughes, 80)...5
Unused Subs: Jermaine Beckford, Ryan Jones.
In deciding how to manage those absentees while obeying competition rules preventing token line-ups, Grayson pieced together the strongest team he could justify while topping up his bench with an untested striker in Davide Somma and a junior goalkeeper in Ryan Jones. The approach paid off but only just.
Among the small but respectable crowd at Elland Road, Jones would have been familiar only to those who followed United's reserve squad closely last season.
United's losses were so severe that even Frank Fielding - signed on loan from Blackburn Rovers specifically to compensate for an injury to Shane Higgs - was stationed elsewhere with England's U-21s, leaving Jones to deputise for Casper Ankergren. It was, to that degree, a case of muddling through.
With every professional available to him, the demands of the Johnstone's Paint Trophy would not have bothered Grayson, but a second-round tie against Darlington in a competition of low priority was not a game his squad needed.
Were it not for the postponement of Saturday's league game at Bristol Rovers, United would have been cursing it. Satisfactory, then, was the win delivered by his carefully-constructed team; less so the performance or the loss of another player - Somma - to yet another injury.
United imposed themselves on Darlington with two goals claimed inside half-an-hour, scored by players who have seen little or no football this season and should feel happier this morning for the chance of acknowledgement. Not all of their team-mates will be so content.
Andy Robinson registered Leeds' first goal and Tresor Kandol their second, a source of confidence for United's winger and a red letter day for the club's striker.
On the last occasion that Kandol scored in a first-team match at Elland Road, Leeds were days away from the 2008 play-off final. It has been that long.
His contribution over 45 minutes may convince Grayson that Kandol is worth more than simply a squad number, particularly while Luciano Becchio deals with an injured ankle. Robinson too enjoyed the type of lively first half he probably needed. To that end, the fixture had its uses, though Grayson made no effort to disguise how angry he was with his team's failure to kill the tie.
Despite the Trophy's meagre profile, its regulations dictated that he field six of the 11 players with most club appearances on their records this season, a requirement that Grayson was able to meet despite making six alterations to the team that drew with Charlton Athletic on Saturday.
Anxious though he was to avoid incurring a fine, Grayson's options were not exactly vast. They did, however, include Kandol, a player who has been virtually anonymous at Elland Road for the past year and a half. Promoted to the starting line-up - an announcement that drew applause from the crowd - his rare inclusion spoke of the lengths his manager had gone to in fulfilling last night's match.
Perspective was still necessary against a club with more endemic problems.
Darlington came to Elland Road as the Football League's lowest-ranked team and one who, until this morning, were technically without a manager.
Steve Staunton, Leeds' former assistant, was appointed on Monday with the intention of taking charge today, and while he attended last night's game, he declined the chance to watch his squad from the touchline, preferring to take a seat in the directors' box.
Ken Bates, the man who ordained that Staunton should take his leave of Elland Road 10 months ago, was not there to greet him.
From that vantage point, Staunton's early viewing was not particularly pleasant.
Darlington made the effort to be expansive and use possession carefully but their defence was only ever one clean strike away from being breached.
Nick Liversedge, their goalkeeper, dealt with one firm header from Kandol by touching it over Darlington's goal and did so again with more urgency when a second header from the striker dropped beneath his crossbar.
Those two efforts materialised inside 15 minutes; by the 20th, Robinson and Aidan White were pulling shots wide from positions where Liversedge would have anticipated having a save to make. No surprise, then, that the damn should burst four minutes later.
A foul on White gave Robinson his first chance to attack Liversedge with a free-kick and his low set-piece crept inside the keeper's near post, carried over the line by a very minor deflection. It should, even then, have been the beginning of a ruthless end.
In the 28th minute, Neil Kilkenny fed Kandol from the halfway line and the forward's screaming shot from the edge of the box ripped into the roof of Darlington's net.
It gave Staunton much to ponder as he prepared to sit down behind his new desk. In Darlington's favour will be their reaction to United's goals and their improvement in the second half.
Caretakers Craig Liddle and Neil Maddison immediately removed defender Matthew Plummer to make space for substitute and forward Mark Convery, and the change brought a goal in the last minute of the first half.
Jamie Devitt, who had earlier curled a wild shot over the bar after Gary Smith cut open the left side of Grayson's team, picked out Convery with a cross which Ankergren failed to reach and Convery side-footed into an empty net.
Darlington's sixth goal of the season did not flatter United's defence.
Kandol was substituted at half-time after illness overcame him, and Enoch Showunmi appeared in his place, a meaningful comparison between fringe strikers with similar attributes.
Forty-five stagnant minutes followed, however, and Convery was inches from equalising at Ankergren's back post with an hour gone. Grayson - aware of the decreasing intensity - was vocal in demanding better from his technical area.
He gave Somma his debut as the game wore on but the contest was petering out, save only for Kevin Gall's shot at one end and a low strike from Showunmi at the other, parried with one hand by Liversedge.
Liversedge's night would later end with a red card, shown to him in injury-time for a professional foul on Showunmi. The unnecessary dismissal came so late that midfielder Jeff Smith, improvising as a keeper, had only one wayward free-kick from Robinson to worry about.
Four minutes before the sending off, United's bewildered staff looked on as Somma collapsed without a player near him and was helped from the pitch, leaving Leeds with no remaining substitutions and 10 players. Somma had appeared from the bench no more than 15 minutes earlier; Grayson could not make it up.
YEP chief football writer Phil Hay rates how Leeds United's players performed against Darlington last night.
Casper Ankergren: His handling on a wet surface was pretty reliable during the game but he seemed to misjudge Devitt's cross when Darlington scored, leaving an open goal behind him...5
Leigh Bromby: Not a great night for Bromby who was hassled incessantly by the visitors and failed to impose himself at right-back. Caught out of position too often...5
Lubomir Michalik: Looks increasingly confident and - step by step - is returning to something like his best form. The pick of the defenders last night and almost scored twice...7
Richard Naylor: His display might have been overlooked amid United's mediocrity, but he won challenge after challenge in the second half and is one player who can hold his head up...6
Andrew Hughes: Did what he always does and kept the door closed down the left flank. Nothing spectacular in Hughes' display but Darlington were never going to score from his side of the pitch...6
Andy Robinson: Enjoyed a very encouraging first half-hour in which he toyed with Darlington and scored the opening goal but the tempo of his display subsided sharply...5
David Prutton: Last night was a chance for Prutton to catch Grayson's eye and one the midfielder failed to take. A frustrating evening when nothing came off and passes went astray...4
Neil Kilkenny: His through ball to set up Kandol's goal was Kilkenny at his best, and there were flashes of the Australian's invention throughout the game. Not as dominant as he can be...6
Aidan White: Used as a left winger, a role he is quick enough and skilful enough to fill, and although White was quiet in parts of the game, his more direct runs gave Darlington trouble...6
Tresor Kandol: It is easy to forget that Kandol is still on United's books, but his goal was superb and he caused no end of problems. A strong claim for more involvement under Grayson...7
Mike Grella: Hobbled off on 70 minutes after a hard, unrewarding shift. Darlington kept a tight leash on him throughout the game and his tireless running did not amount to much in return...5
Substitutes: Enoch Showunmi (for Kandol, 46)...5
Davide Somma (for Grella, 70)...5
Bradley Johnson (for Hughes, 80)...5
Unused Subs: Jermaine Beckford, Ryan Jones.