The Republic of Ireland U-21s fell to defeat in Sofia, when a goal in either half gave Bulgaria a 2-0 victory.
Goals from Atanas Kurdov and Momchil Tsvetanov condemned Ireland to defeat in this UEFA U-21 European Championship qualifier.
Defeat means the Irish sink to the bottom of a group which also includes England, Portugal and minnows Montenegro.
Manager Don Givens restored Owen Garvan and Sean Scannell to the side after they missed last month's friendly in Austria while Sligo Rovers defender Seamus Coleman kept his place at right-back.
Blackburn trio Nolan, Keith Treacy and Alan Judge all started and there were places on the bench for Shamrock Rovers pair Simon Madden and Padraig Amond.
The match kicked off in intense heat and despite an attacking start from the visitors it was Bulgaria who had the first real attempt in the 20th minute.
Lachezar Baltanov created a shooting opportunity and struck an ambitious 35-yard effort but it was comfortably saved by goalkeeper Shane Redmond.
The home side took the lead on the stroke of half-time. Tsvetanov broke down the left and pulled the ball back to Kurdov, who turned and shot low into the far corner.
Owen Garvan was denied the opportunity to draw matters level straight after the re-start when he narrowly failed to connect to Sean Scannell’s through ball.
Moments later, Treacy drilled the ball across the face of the goal as the Irish pushed for an equaliser.
Ireland captain Eddie Nolan had the next chance of the game when he headed over from Seamus Coleman’s free kick on 56 minutes.
Despite applying a degree of pressure, it was the home side who were to get on the scoresheet again. In the 77th minute, Tsvetanov drifted in from the left and drilled his shot low into the Irish net.
Bulgaria: Nikolay Mihaylov (capt), Pavel Vidanov, Nikolay Bodurov, Ivan Ivanov, Viktor Genev, Lachezar Baltanov (Atanas Zehirov, 76 mins.), Maryan Ognyanov (Nikolay Diulgerov, 36 mins), Atanas Kurdov, Biktor Petakov, Nikloay Chipev, Momchil Tsvetanov (Todor Kolev, 82 mins)
Substitutes not used: Maryo Kirev, Todor Stoev, Kostadin Gadjalov, Ivan Tsachev
Republic of Ireland: Shane Redmond, Seamus Coleman, Michael Liddle, Eddie Nolan (capt), Darren Dennehy, Jimmy Ryan, Alan Judge, James Berrett (Padraig Amond, 69 mins.), Sean Scannell, Owen Garvan, Keith Treacy
Substitutes not used: Stephen Henderson, Stephen Gleeson, Simon Madden, Brendan Moloney
Referee: Marco Borg (Malta)
