It is another frantic weekend even by the standards of Lothar Matthäus's nomadic lifestyle. On Friday the 50-year-old was looking dapper on a Uefa stage in Monaco, drawing his former club Bayern Munich into what Germans are naturally dubbing the "Todesgruppe" (group of death) alongside Manchester City in the Champions League. Saturday: a quick stopover in Munich, where he currently lives, almost out of a suitcase, before jetting off to Bulgaria on Sunday morning. There is a bit of time to talk now, he says, sounding a little tired on the phone. Fifteen minutes by himself in a hotel room in Sofia is as good as it gets these days.

This coming Friday Bulgaria, coached by Matthäus, will take on England in what may be the most important match of the German's managerial career. There is the small chance that Bulgaria, six points adrift of the joint-leaders, England and Montenegro, in fourth place, could still make it to Poland and Ukraine. "We shouldn't start looking forward to the World Cup [2014 in Brazil]) as long as there's still a possibility to qualify for the Euros," he insists, "there is no reason to give up just yet. I always believe."But perhaps more importantly for Matthäus personally, it offers a shot at redemption.

Slaven Bilic and Guus Hiddink can testify to the transformative nature a victory against England can have. It can validate and define a manager at this level. Bulgaria seem content enough with his 11-month tenure – unbeaten in three competitive fixtures – to keep him in the job for two more years but Matthäus could do with a marquee result.

Coaching an underdog to an upset against the fourth-best team in the world, if Fifa is to believed, would really stick it to the many doubters at home and go some way to improve his standing there. While Matthäus is at pains to stress that Friday's match "is not about me against England or Fabio Capello, it's about Bulgaria, and I would be just as motivated if we played a lesser team" he must be keenly aware that the match offers a tantalising glimpse of a respite, perhaps even an end to his 11-year odyssey through football's more exotic regions.

The 1990 World Cup winner and holder of 150 international caps has been constantly on the go since quitting his playing career, aged 39, trying his luck with Rapid Vienna, Partizan Belgrade, Hungary, Atlético Paranaense, Red Bull Salzburg and Maccabi Netanya in the process. None of these lasted beyond a season and each adventure led him further from his desired destination: to coach and prove himself in Germany.

He has thrown his hat in the ring for various jobs more often than anybody cares to remember over the last decade. But despite the best efforts of Franz Beckenbauer, who continues to support his former captain publicly at any opportunity, nobody wants to bet on him, not even in the lower leagues. "The clubs," one well-connected German agent explains, "see him as a kind of security risk. They're wary of his notoriously close relationship with Bild, the leading tabloid, and don't want the kind of attention that has come with him in recent years."

The four-times divorcee has, by virtue of being a little too forthcoming in media interviews, become a darling of the gossip magazines. They have chronicled each and every detail of his seemingly constant relationship troubles with relish and, with every new girlfriend or ex-girlfriend exposé, Matthäus the world-class player has given way a little more to Matthäus the celebrity in the eyes of his compatriots. As a consequence he has been forced to seek out relatively obscure offers abroad, where his stature is far less diminished.

The past, unfortunately, has provided no refuge either. If he had been born and achieved the same in any other country, Matthäus would have been feted, knighted, loved forever. But German football is unforgivingly pragmatic, almost completely devoid of nostalgia. If anything, his few failings have increasingly become better remembered.

The self-imposed substitution five minutes before time in Bayern's 2-1 Champions League final defeat against Manchester United, for example, led to him being called a bottler by his former team-mate Mehmet Scholl. It is a charge that resonates, unfortunately. His decision to pass on penalty-taking duties to Andreas Brehme in the 1990 final when Matthäus felt unhappy in a new pair of boots has been looked upon more unkindly with each passing year. German football indulges oversized egos but not those who decline to take responsibility.

Former heroes on the pitch need to be successful off the pitch, too, and quickly, to avoid becoming an irrelevance, or worse, an embarrassment. Matthäus, locked out of his own fiefdom after falling out with Bayern over the precise financial terms of his testimonial – "I was badly advised at the time," he offers, with genuine regret – has spoken from the sidelines in ill-conceived magazine columns whose damage to his own cause remain severely underestimated. "I've never understood why people take such offence, it's just my opinion," he says. "It's harmless stuff."

What of England then? "They have great individuals but lack stability as a team compared to Spain, Germany or the Netherlands," he ventures carefully. Matthäus is also unsure whether they have made genuine progress since the World Cup, where he witnessed their demise at the hands of Germany as a pundit for al-Jazeera.

"They seemed tired and unable to deal with the great expectations in South Africa," he says. "And you could also see how the pressure got to them in the games against Montenegro and Switzerland at Wembley. I find it very hard to understand. Playing in such a stadium at home should give you a lift. It should be like a fortress. Instead they have done much better away from home. Their performances and results [outside England] have been excellent."

One senses that he would rather play at Wembley, a ground he associates with happy memories. "I played there for the first time in 1982. We won 2-1 thanks to two goals with Karl-Heinz Rummenigge," he recalls, suddenly beaming with pride.

A player-by-player comparison does temper his optimism for Friday night somewhat ("I know where they play and I know where our guys play, one has to be realistic about the difference in class") but he has upset the odds against English opposition once already, it is worth remembering. In August 2003 Matthäus led his unfancied Partizan Belgrade past Bobby Robson's Newcastle into the group stage of the Champions League, appropriately enough via penalties. The result arguably remains the high point of his managerial career to date, which is to say that it proved something of a false dawn. The more he talks about Friday's match, however, the more he seems to convince himself that another surprise is possible – especially if England start second-guessing themselves again. "We will give it a go in front of our supporters, in the knowledge that all the pressure will be on them to win," he says. "They need to stay ahead of Montenegro, who are in hot pursuit, and get maximum points before the key match [in Podgorica]. "Maybe we can catch them out ."