It’s been 17 years since the men’s senior team set foot in the Eastern European nation. Last time it heralded the end of the Berti Vogts era. Tomorrow’s match could equate a near role-reversal for current incumbent Steve Clarke, who will reach deity levels if he can become the first Scotland manager since Vogts (excluding Nations League help) to qualify for a international tournament play-off round and complete the mission of reaching Qatar 2022. All that is needed to complete step one of that route is a victory on Friday evening.
Things will have to go better than they did in Chisinau on a chilly and damp night in October 2004. Steven Thompson, once of Rangers and now of Sportscene fame, managed to drill in a quick equaliser after Serghei Dadu gave the hosts a 28th-minute lead. But that was all Scotland could muster as they limped to a 1-1 draw which, coupled with taking one point from two home games to begin the group, was enough to send the travelling fans over the edge and seal Berti’s fate.
Former Hibs star Ian Murray featured that night. Still in his first spell for the club before a move to Rangers, Murray had only just returned from a lengthy knee injury when he was surprisingly called up to the squad and then subbed on for the second half after injury forced off ex-Hearts left-back Gary Naysmith.
Not exactly ideal circumstances to earn the first of two competitive caps in a Scotland jersey, but as the former player explains, you ecstatically grasp the chance to represent your country whenever the opportunity comes.
"It was a tough night, that one,” Murray recalls. “I remember it being cold and the pitch was fairly poor. They were a decent side. We didn't play very well and there were a good few scares as we managed to get away with a draw.
“The mood was fine while we were away despite the struggles. On international trips everyone is excited for the break from club football and want to realise a dream of playing for your country, regardless of where and when it is.
“We certainly didn't go into the game expecting not to win, but we knew the Moldovans were an emerging side. They had some decent players and it was quite a hostile place to go.
“Berti was going through a tough time, as were the players, while the fans were particularly unhappy. So it's a stark contrast to what the guys are going into this time around.
“Scotland are in much better shape than when we went there and they've got the incentive of finishing in second place, something we didn't really have in our grasp at that point.”
Flying off to unfamiliar parts of Eastern Europe (and beyond) is no longer the apprehensive step into the unknown it used to be viewed. The expansion of European football over the years will mean the vast majority of Scottish stars, if not Moldova itself, will be used to similar in terms of long travel and difficult terrain.
“The current group are well-versed in travelling all over Europe, so there’s not much advice I can give them,” admits Murray.
“I was fascinated by the place. It was completely different to Scotland. Not just the pitch, stadium and facilities but also the surrounding areas as well. It was often quite dark, all the street lamps were quite small, and there wasn't a whole lot to do around about where we were staying. But I knew it was an emerging nation, not just in terms of football but culturally as well. I always wanted to go back, just never had the chance.
“They've improved a heck of a lot, which doesn't surprise me. They're technically good footballers across that side of Europe. It's one of those countries where you're always going to get one or two, maybe three, really good players, but due to the size of the nation it is difficult to keep producing them.
“I think people underestimate them. I don't think it'll be an easy game, I really don't, even though they've not had a great qualifying campaign.”
One of the toughest selection dilemmas for the Scotland boss prior to Friday’s match centres around a player from Murray’s former club.
Kevin Nisbet started the last time Scotland faced Moldova in the 1-0 victory at Hampden in September, though the Hibs striker didn’t have the best of performances and has subsequently played just nine minutes over the following three international fixtures.
The inclusion of Stoke City striker Jacob Brown has further complicating matters with the 23-year-old scoring three times in his last six matches in the English second tier, while Nisbet has netted only once since August. The Easter Road star, however, does retain a significant advantage.
“It's a tough one for the manager,” admitted Murray, currently boss of cinch League One leaders Airdrieonians.
"In Brown, you've got someone new coming into the squad. In Nisbet, we've got someone we know can perform. I haven't seen much of him this season, though from what I hear his recent form has not been fantastic.
"These are the stages you get judged on as well. With no disrespect, scouts don't come to watch you for the matches against the likes of St Mirren or Ross County, it's the matches against Celtic or Rangers or playing for the national team. That's where you need to perform.
“Personally, if Clarke goes with two, I think he'll go with Nisbet. He's got that extra experience at the international level, and we know Kevin's got the capability of scoring on his day. He's got great movement and he's a really good finisher. I just hope he's mentally ready for the game.”