Six years ago John Toshack, the man Brian Flynn replaced in the Wales hot-seat, began his managerial reign with a comfortable victory over a side led by Lothar Matthäus.
The former Germany captain was not so accommodating to Toshack's stand-in replacement night. Craig Bellamy's double at the Millennium Stadium marked that first match in charge. There was no Bellamy, deemed unfit despite returning after a month lay-off last week, to rescue Wales here.
There was also no new man to save Wales in an all too familiar miserable outcome. If the rows of empty seats at the Cardiff City Stadium didn't tell its own story, Wales have seen their Euro 2012 campaign all but ended just two games into the latest qualifiers.
Along with Wales' chances, Brian Flynn's prospects of landing the full time job he so craves may have taken a nosedive following Ivelin Popov's second-half winner for Bulgaria.
"It was a painful and disappointing result, but I've learned so many lessons. I have found things out in the heat of the battle but the chances of qualifying are very doubtful. My plan was to get six points [from here and Switzerland]. Personally, I think it has dented my chances of getting the job full-time."
This was billed as a whole new era for Wales. A "licence to thrill" was the pre-match soundbite reverberating around the Wales camp ahead of Flynn's two-game trial. But once Chris Gunter failed to hand Wales an early lead, the writing was on the wall between two struggling nations.
Scoring goals was a problem under Toshack and it seemed to have caught on under Flynn. Gareth Bale and Steve Morrison had chances to have given the disjointed hosts a first-half advantage, before Popov found room to fire home the 48th-minute winner.
Wales huffed and puffed as they threw men forward, but after substitute Hal Robson-Kanu wasted a late chance, Gunter's night went from bad to worse when he was sent off for tripping Dimitar Rangelov as he bore down on goal in added time. "We have to start again now," added Flynn. "But I have faith in my players."
Wales (3-5-2): Hennessey, Gunter, Danny Collins, James Collins, Ricketts, Ledley (King, 59), Edwards (Church, 69), Williams, Bale, Vaughan, Morison (Robson-Kanu, 82). Substitutes not used Myhill (gk), Blake, Ribeiro, Crofts.
Bulgaria (4-4-2): Mihailov, Zanev, Iliev (Vidanov, 37), Bodurov, Ivanov, Peev (Rangelov, 72), Georgiev, S Petrov, M Petrov, Makriev, Popov. Substitutes not used Stoyanov (gk), Angelov, Yankov, Domovchiyski, Dimitrov.
Referee J Eriksson (Sweden).