Having taken charge of his old club with the intention of turning them into title challengers again,
will get his first real indication of the task he has undertaken tonight when
City take on current champions St Patrick’s Athletic at Turner’s Cross.
The home side are hampered by injuries to Danny Morrissey and Michael Rafter and might still have the look, the manager suggests, of a work in progress when compared to the Dubliners, but the former striker will hope to inspire the sort of performance that made the teams he played in so formidable more than a decade ago.
Much may depend on Anthony Elding, with Caulfield keen to see the big striker make something resembling the remarkable start he made to last year's campaign at Sligo.
Beyond that, he says, he is confident about the group he has assembled over the past few months even if, he insists, they are still in early stages of building something significant for the future.
More immediately, he admits, tonight's opponents will be a serious step up on what his players have been used to in recent weeks. "We're not in the Setanta Cup and we haven't been able to get Premier Division clubs down here for friendlies so, with all due respect to the clubs we have played, St Pat's will certainly represent a tougher challenge."
Liam Buckley has a full-strength squad to choose from and the champions have a good record in Cork lately, with their only defeat in four coming at the tailend of last season after the title had been secured.
Dundalk head to Drogheda without Keith Ward while Stephen Kenny has concerns about Richie Towell and Brian Gartland (both ankle), but it still looks like a daunting opener for a heavily remodelled home team and its manager Robbie Horgan, who must weigh up the fitness of Paul Crowley, Cathal Brady and Philly Hughes before settling on his team.
Stuart Taylor has everyone available to him as Limerick, fresh from their pre-season stint in Spain, host Bray but Alan Mathews has a whole string of problems to contend with, including injuries to Shane O'Neill (groin) and Adam Mitchell (hamstring) and the suspensions of Graham Kelly, Shane O'Connor and Dave Scully.
In the night's other top flight game, Aaron Callaghan kicks off his first campaign with UCD against former club Bohemians. Owen Heary has strengthened the visitors' squad with the addition of Paddy Kavanagh, Aiden Price and Jason Byrne and all are available for a game that will provide an interesting early indication of how two of last season's strugglers are likely to get on this season. Anto Murphy, though, will miss the game with a hamstring problem.
Shelbourne get their chance to bounce back from relegation with a home game against Wexford Youths but the highlight of the night in the first division is the debut of Galway FC against Longford Town.