This time last week he expected to be plotting Gillingham's downfall in the Second Division. This afternoon, instead, he will be trying to arrest Villa's fall against Liverpool and, with all due respect to the Gills' Adeola Akinbiyi, he is no Michael Owen.
If Gregory feels it is strange he has replaced Brian Little, he is not alone. The Villa fans are wondering, too, why a man who was sacked by Portsmouth and has spent 16 months taking Wycombe to mid-table obscurity is qualified for one of the biggest managerial jobs in English football, and there will be pressure on the new man today. Not just to stop the club being embroiled in the Premiership's relegation battle but to justify his appointment.
It could be a baptism of ire if Villa go down to their fifth defeat in six League matches but yesterday Gregory, a former player and part of Little's management team until October 1996, was, naturally, upbeat. "I will do whatever it takes to win a game and ensure our Premiership survival," he said. "But I also like to be entertaining and there are enough people in the side who know how to pass the ball.
"Apart from Stan Collymore and Simon Grayson, it is very much the same set of players who were here before I left. They don't have any less ability than they did two season's ago."
Roy Evans might demur. Two seasons ago his Liverpool side appeared to be heading for great things, disappointment being the only one that has lived up to the bill. Lose again today and even qualification for the Uefa Cup might look difficult but at least the match will be played with knowledge of the result from Stamford Bridge.
Chelsea meet Manchester United at 11.15 this morning and the pack chasing the latter, of which Liverpool are a part, will have torn emotions. If United are to be caught then their defeat is an imperative. On the other hand, if they are going to run away with the title anyway then it would be preferable if Chelsea suffer a reverse.
In contrast there will be unequivocal emotions at the Bridge, where Chelsea will be desperate to avenge last month's 5-3 defeat there in the FA Cup. No time would appear to better than the present because United's squad has the appearance of being held together with bits of string such are their injury problems. At a pinch, Alex Ferguson might risk players like Paul Scholes, Nicky Butt and Ronny Johnsen but with a European Cup quarter- final in Monaco on Wednesday he will probably think the gamble is too great.
Everton are another team hoping to avenge an FA Cup reverse, although the visit of Newcastle will bring diverse sub-plots with it. Gary Speed, the erstwhile captain at Goodison, is guaranteed a hostile reception while Alan Shearer would like nothing more than to score his first League goal of the season at the ground where he suffered the ankle injury last July which cost him five months of opportunity.
Blackburn, a club chasing Manchester United, entertain the Fagins of the Leicester who have become experts at picking up a point or two in their travels, having lost away only four times this season. The home side - no wins in five matches - must also overcome the absence of the suspended Kevin Gallacher.
Leeds have absentee problems for their home game against Southampton. David Wetherall, Alf Inge Haland and Lee Bowyer are suspended, Lucas Radebe is away with South Africa and David Hopkin, Lee Sharpe and Derek Lilley are injured. "We'll have a head count and whoever is available will play," their manager, George Graham, said.
The new pounds 1.3m signing, Martin Hiden, could be among them.
Following Wednesday's win over Manchester United in the FA Cup, Barnsley come down to earth against Wimbledon. They are unbeaten at home since November but are five points adrift of safety at the bottom of the table and manager Danny Wilson, once the midweek euphoria had dissipated, commented: "If I said I would swap everything in the Cup for the points, people would say I'm a miserable bugger. Well that's the way I am because we earn our living in the League."
Coventry travel to Crystal Palace hoping to extend their club record six successive victories while Derby, another team with Europe unexpectedly coming into focus, entertain Sheffield Wednesday.
Tottenham and Bolton are unlikely to require much motivation tomorrow at White Hart Lane. Defeat for Spurs would drop them into the bottom three while the visitors cannot allow a gap to appear between themselves and the fourth-bottom team. And John Gregory thought he was under pressure.Reuse content