Bohemian FC v Shamrock Rovers, Dalymount Park, 7.45pm
Both sides have made ideal starts to the season and occupy the top two spots in the league table, albeit at a very early stage, which only makes this hotly anticipated sellout all the more enticing.
Bohs enjoyed (and that's certainly the right verb) supremacy in this fixture last season, winning three and drawing the other of the four Dublin derby encounters last season.
The northside club have yet to concede a goal this season, with 1-0 and 2-0 wins respectively over newly promoted Finn Harps and UCD. The visit of their imposing southside rivals represents by far their stiffest task so far.
Rovers nudged above them to the top of the table on goals scored following their 2-0 win over Derry City on Friday night. Stephen Bradley's side weren't always at their most fluid but never seriously looked in danger of missing out on the three points.
Wins away to Waterford and at home to Derry City are not to be sniffed at and suggest that Rovers, who have often flattered to deceive, could be in rude health for the 2019 season.
Bohemians: Michael Barker (hamstring), Promise Omochere (ankle) and Cristian Magerusan (cruciate) remain out. Kevin Devaney (knee) remains a doubt.
Shamrock Rovers: Dylan Watts went off with a knock against Derry and will be checked on before the Bohemians game.
Keith Long (Bohemians): "We're in a good place and it's great to have points on the board but Rovers are a different proposition. There is an expectancy there for them to challenge and win titles so we have to be at our very best against them.
"It's a big step-up again and a different test for us but we're looking forward to it. It's a quick turnaround playing Friday to Monday but it's the same for both teams and we haven't had to travel."
Stephen Bradley (Shamrock Rovers): "We’re delighted with the win [against Derry] because at the start of the season you’ll get scrappy games like that and it’s important to pick up three points and we did.
"There’s a few things we’ve looked at from the Bohs games last year, things we could have done better and hopefully we can put them right on Monday night.
"They’re big games the derbies but we need to play our own game. We need to make sure we’re ready for whatever the game throws up, whether it’s a battle or a football match."
Derry City v Waterford FC, Ryan McBride Brandywell Stadium, 7.45pm
Both teams have a win and a loss apiece but Waterford enter this encounter on a high following their successful raid on Turner's Cross last Friday.
Two injury time goals, one in either half, through Bastien Hery and Zack Elbouzedi enabled Alan Reynolds's side to bounce back from their opening night loss at home to Shamrock Rovers in the RSC.
It was Rovers who accounted for Derry's first defeat of the season, with Devine's side going down 2-0 at Tallaght Stadium last Friday. Their mood won't have been cheered by the sight of old boy Aaron McEniff sealing Rovers' victory with a Panenka penalty late in the game.
Still, it's back to the Ryan McBride Brandywell tonight, where their record remain formidable, even during last year's difficult campaign.
Derry City: Centre-half Darren Cole (calf) missed Friday night's loss at Shamrock Rovers, but will have a late fitness test before kick-off. Jamie McDonagh is suspended.
Waterford FC: JJ Lunney is doubtful while Izzy Akinade and Scott Twine are expected to miss out. Georgie Poynton has also joined the squad.
Declan Devine (Derry City): "They're a really good side," he told the Derry Journal. "In my opinion they are one of the favourites to win the league. It's going to be a battle at times but both teams will want to get the ball down and play."
Alan Reynolds (Waterford FC): ""The result [against Cork] was fantastic, but I thought that the performance and display from everyone was outstanding. We deserved it and it could have been more. We were really good and if we were more clinical in front of goal we could have scored more.
""Declan [Devine] has put together a really strong side so we know we’ll be in for a tough game on Monday. It’s a long journey, especially with a short turnaround, but we’re looking forward to it and have prepared the right way."
Dundalk v UCD, Oriel Park, 7.45pm
A bumpy opening to the season for both these sides.
The Premier Division champions had to come from behind to nab draws against Sligo Rovers and Finn Harps, as they make a faltering start to life after Stephen Kenny.
While the First Division champions have found the going immediately tough with Collie O'Neill's side shipping bad defeats up in Derry and then at home to Bohemians last Friday.
Dundalk: Jamie McGrath returns to the squad while Joe McKee is available after his loan move from Falkirk. Patrick McEleney and Robbie Benson are ruled out through foot and leg injuries respectively.
UCD: To come
John Gill (Dundalk): "We have a lot of quality, we know what we are about and we would liked to have got the wins but we are looking forward to the game tomorrow night. It’s going to be tough."
Sligo Rovers v Cork City, The Showgrounds, 7.45pm
Two sides still seeking a first win of the season meet in the Showgrounds on Monday night. Cork City fans may be slightly more surprised to see their team in this position, given the last few years of contesting, and occasionally winning, the league title.
Indeed, Caulfield's side have yet to rattle the net this season, falling 1-0 against the Sligo Rovers old boys club in Inchicore on the opening Friday and then slumping to a 2-0 home defeat in the Munster derby against Waterford FC. Their manager admits there are problems in the goalscoring department right now.
Sligo, on the other hand, have made what many would constitute a reasonable start given their treacherously difficult programme early doors.
After an impressive 1-1 draw in Oriel Park on the opening night, they appeared set to hold the promising St Pat's outfit scoreless in the Showgrounds on Friday but for a sickening last-gasp winner for the away side, not made any more palatable by the identity of the scorer, former Sligo player Mikey Drennan, who wasn't minded to eschew celebration afterwards.
Sligo Rovers: In injury news, Johnny Dunleavy (groin), David Cawley (knee) and Ronan Murray (ankle) are all doubtful.
Cork City: Alan Bennett will miss out with a hamstring injury he picked up on Friday against Waterford, with Matthew Gilliam still sidelined after a pre-season injury. Caulfield also has question marks over the availability of Gearoid Morrissey, Shane Griffin and Graham Cummins, all of whom will be assessed prior to the game.
Liam Buckley (Sligo Rovers): ""The goal in the last minute (against St Pat's) killed us. I thought we put in a reasonable shift from a work point of view. There wasn’t a lot between the two teams, I don’t think either deserved to win considering how the way the game went.
"Looking at the game, Pat’s had a bit of possession and we had a bit of possession. We just need to be better on the ball. I’ll be honest; we haven’t seen the best of this group as of yet because technically they are very good and we just need to stamp our style on the play.
"We’ve emphasised that again on Sunday in relation to playing on Monday. We need to get our personality in the game and if we do get the best out of the lads from a collective point of view I think we’ll have a good season."
John Caulfield (Cork City): ""Sligo is always a difficult challenge; the games are always very tight up there. We know we need to play very well, obviously we know we need to score, so it’s a very, very difficult game.
"That’s the way the league is this year, for a lot of teams, there isn’t a lot between them and on the night, you just need to hit form. A lot of the games between us have been draws, yes, we have won a few up there, but they go to the wire.
"Sligo is a fantastic football town and county, they get right behind their team. It’s a passionate and hostile place and we need to give a top performance."
St Patrick's Athletic v Finn Harps, Richmond Park, 7.45pm
Two 1-0 wins have Pat's up among their city rivals on six points after two games. New signing Mikey Drennan struck the winner in both games, the first from the penalty spot in a scrappy opener against Cork and the second a last-gasp winner against his old club Sligo Rovers on Friday, something which stuck in the craw of the home support.
It’s a quick turnaround for Harps after the energy sapping draw with Dundalk at Finn Park on Friday night. One point on the board may not seem too hectic but it's a reasonable return considering the daunting nature of their opening to the season.
Recovery for their part-time squad is a key concern for Ollie Horgan but he isn't inclined to use it as an excuse heading into Monday's encounter.
St Patrick's Athletic: Gary Shaw has recovered from a hamstring strain. Dean Clarke is still out with a leg injury.
Finn Harps: Harry Ascroft and Mark Timlin are injured while Mark Coyle is a doubt after struggling in the closing stages against Dundalk.
Harry Kenny (St Patrick's Athletic): "Ollie Horgan always has his team well organised and we know that they will come to Inchicore really fired up and focused on getting a result. From our end, we just want to keep things going and add to our points tally."
Ollie Horgan (Finn Harps): "We just have a point from two matches. We haven’t done badly performance wise but we need to get some more points on the board early to give the lads a bit of confidence. While it was great to get the draw against Dundalk, it was hard earned and we’ll only see when the final whistle blows tomorrow night whether the physical toll from the quick turnaround in games was too much or not."
"Pat’s are up there at the top with Shamrock Rovers and Bohemians. We’re five behind that so we’re going to Richmond Park to get a result against a side that hasn’t conceded a goal in the games against Cork and Sligo. Getting a bit more going forward will be needed and hopefully some of our attacking players can find the back of the net tomorrow night.