Holders Shelbourne must overcome Dundalk at Oriel Park if they are to stay on course for a third Harp Lager FAI Cup triumph in a row.
The Dubliners, who have already played Jim McLaughlin's side four times this season, were handed one of the toughest assignments of the second round draw - although even they may take some consolation from the fact that they have avoided Derry City's fate - a trip to Turners' Cross.
"This is probably the most difficult draw of all," said Derry manager Felix Healy after hearing the draw. "It's extremely difficult but we've gone to Cork before and won so they'll be looking for revenge."
That tie will a repeat of last season's quarter-final at the Brandywell where Derry won 1-0. Derry also beat Cork by a single goal in the 1989 final when Dave Barry played for the southerners and Healy scored the winner for the current league champions.
The pairing of Dundalk and Shelbourne, meanwhile, is a rerun of the 1993 final, won by the Dubliners, as well as last year's second round clash at Tolka Park which the home side won by four goals to two.
This year the clubs have met four times, twice in the league and twice in the two-legged league cup semi-final. Damien Richardson's team have won on all four occasions.
"They've beaten us four times already this season so we'll certainly know what to expect," chuckled McLaughlin last night, "but I don't mind, this doesn't worry me at all.
"They've progressed over the last few years to the point where they're one of the best teams in the country while we've only started to get our act together over the past six months so it'll be up to us to raise our game to their level but we'll be well prepared," he said, before adding that "we have nothing to lose so we'll be looking forward to it."
Richardson gave the news a cautious response, remarking that "It's a demanding task for us but with Shelbourne being the cup team of the nineties and their great record over the years in the competition, I suppose it has the makings of a cracking draw."
The Shelbourne manager conceded that his main hope was to avoid being drawn away to Dundalk, St Patrick's Athletic, Derry or Cork. "As the balls were running out I realised the likelihood of getting one of them was increasing, then Cork and Derry came out and I though "well, that's them out of the way" but as it's ended up this is fairly much as tough as it could have turned out for us."
Elsewhere two first division sides were drawn at home to teams from the top flight while a third, Cobh Ramblers, will take on either Waterford United or St Patrick's Athletic at St Colman's Park.
Athlone Town must wait until Wednesday night to find out whether their home tie will be against Shamrock rovers or Drogheda United, while Galway United will take on Finn Harps at Terryland Park.
For us the priority would have been to get a home draw," said Harps manager Charlie McGeever last night, "but Terryland isn't too far away which is a bit of a help.
"Overall," he commented, "it's probably a good enough draw for us. I haven't seen that much of the first division this season.
"Bray are a good enough team and so are Waterford but after that there seems to be a bit of gap. It'll be interesting to go to Galway again, as well, they came down as we went up a couple of years ago so it'll be our first visit there in quite a while."
If Longford Town can overcome Wayside Celtic in Wednesday's first round replay they will meet another non-league club, Whitehall Rangers, while a Sligo Rovers victory over Mervue United in their replay would pair them with 1990 finalists St Francis.
The last tie of the round, the only one to take place over the weekend of February 8th, involves UCD and Home Farm Everton, with home advantage going to the students.
