Drogheda United v UCD - United Park, 8.0
Perhaps a tie neither side would have wished for, but an intriguing one all the same with Drogheda, second in the First Division, quietly confident they can cause a minor upset against a UCD side managed by Paul Doolin, a six-times FAI Cup winner.
"It's not the glamour tie we could have got but I'm nonetheless delighted with it," says Drogheda manager, Harry McCue.
"We're at home to a Premier Division team that's in good form.
"We fancy ourselves a little. We're going well and have a nice young team."
It's a good opportunity to gauge ourselves against a good, well-organised Premier Division side".
Drogheda are hampered by suspensions to three key players: Goalkeeper Gary Rogers, defender Danny O'Connor and midfielder Dom Tierney.
Under-21 goalkeeper, Jason Lowney, takes over in goal while Alan Dodd, David Kelly and Robbie Coyle are all in contention to start.
UCD have appealed Clive Delaney's three-match suspension and he's likely to be available to renew his central defensive partnership with captain Tony McDonnell who returns from his one-match ban.
Referee: I Stokes (Dublin)
Betting: Home: 7/2; Draw: 9/4; Away: 4/6.
Glenmore Dundrum v Dublin City - Whitehall, 7.45
Even the bookies fancy this one as a potential shock. And Glenmore Dundrum player/manager, Joe Reynolds, has no problem with that.
"Without being in anyway cocky or disrespectful to Dublin City, I think we've a chance," says Reynolds, optimistically. "They are top of the First Division and are having a good season. Johnny McDonnell is doing a great job. But we feel we can give them more than a match. We are under no illusions, though. We will have to play very well to have any chance of causing an upset. But we are in good form and they will have to be on their game to beat us."
"I'll be telling my lads that there is nothing to be afraid of," adds Reynolds. Midfielder Derek Dodd, one of seven former National League players in his team, is Reynolds' only concern but should overcome a hamstring strain.
Dublin City are without defender Graham Doyle (neck) while fullback Stephen Gifford is hoping to be fit following a back strain. "We've struggled against the likes of Limerick and Cobh so we must guard against under-estimating Glenmore because they are good enough to punish us," said Dublin City manager, John McDonnell.
Referee: H Byrne (Dublin)
Betting: Home: 2/1; Draw: 2/1; Away: 5/4.
St Patrick's Athletic v Bray Wanderers - Richmond Park, 7.45
Both sides would have much preferred non-league or First Division opponents at this stage of the competition.
As it stands, one of the top six tips is going out at the first stage with complacency certainly not a factor for either.
"It's a very tough draw as you can never be off guard against Bray," said St Patrick's coach Eamonn Collins. "You can never be complacent against Bray, not that we'd be complacent whoever we play. We are at home and must make that advantage pay. It's very much a game we're looking forward to."
Midfielder Paul Osam (knee) and striker Kevin Doyle (ankle) should be fit to start again. Liam Kelly is not so fortunate as he remains sidelined having missed last week's win over Dundalk with an ankle injury.
Bray remain without striker Jason Byrne who continues his recuperation from a groin strain sustained against St Patrick's when Pat Dolan's side won 2-0 at the Carlisle Grounds a month ago.
Despite having both Dave Campbell and Davy Williamson available again following injury, manager Pat Devlin is unlikely to make any changes to a side that haswon their last two games scoring eight times without reply.
Referee: R O'Hanlon (Waterford)
Betting: Home: 11/4; Draw: 2/1; Away: 9/4.