Cork City will begin their quest to retain the FAI Cup with a third round Munster derby clash away to Limerick 37.
New Republic of Ireland manager Giovanni Trapattoni was assisted in making the draw by right-hand man Marco Tardelli this evening and the Italian pair produced some intriguing ties.
Cup specialists Longford Town will make the trip to Inchicore's Richmond Park to face current league leaders St Patrick's Athletic, while Jeff Kenna's Galway United will have their work cut out when Waterford United visit Terryland Park.
For Sligo Rovers there is an away tie against Shamrock Rovers, while Bohemians hosts Drogheda Town and Shelbourne will welcome Dundalk.
Newly crowned FAI Intermediate Cup champions Rockmount will have the visit of Bray Wanderers to look forward to, in what could prove a tricky tie for the Premier Division side.
Fellow non-leaguers Fanad United face an away trip to Kildare County, while Cork's Douglas Hall will have the honour of hosting eircom Premier League champions Drogheda United.
There were bitter sweet draws for four other non-league sides involved who will not enjoy big pay-days but see their chances of progressing enhanced by drawing fellow minnows.
Cork side Everton will host Shannon-siders Carrick United, while St Mary's face Wayside Celtic.
Ties will be played on the week ending August 19th.
Wexford Youths v Killester United
Galway United v Waterford United
Douglas Hall v Drogheda United
Everton v Carrick United
Shelbourne v Dundalk
Rockmount v Bray Wanderers
Monaghan United v UCD
Limerick 37 v Cork City
St Patrick's Athletic v Longford Town
Kildare County v Fanad United (Donegal)
Athlone Town v Finn Harps
Derry City v Liffeys Pearse
Sporting Fingal v Cobh Ramblers
Bohemians v Drogheda Town (Terry
Shamrock Rovers v Sligo Rovers
St Mary's v Wayside Celtic