But Oliveira's passion and attack-minded football paid off in the qualifying stages as Portugal finished top of their group.
Many observers agree that the skills of the national coach, now in his 50s, have ripened during his second stint in charge.
Oliveira has become shrewder and perhaps less aggressive than he once was, relying more on the subtlety of his tactics, but playing attractive football is still the number one priority.
"We want to win and entertain the crowd at the same time, because the fans are the true essence of football," he said earlier this year.
Oliveira learnt his attack-minded style from another former Portugal coach Jose Maria Pedroto during his playing days at FC Porto in the late 1970s.
He went into coaching as a player/manager in his hometown club Penafiel in 1981, but it was not until he moved to Sporting Clube de Portugal that he won his first trophy, the Portuguese Super Cup.
Spells followed at Maritimo, Vitoria Guimaraes, Gil Vicente FC and SC Braga, as well as with the national under-21 squad before taking over the senior team in July 1994.
Two years later, Oliveira resigned amid sleaze allegations and in the wake of Portugal's 1-0 loss to the Czech Republic in the quarter-finals of Euro 96.
But he soon returned to form at club level, steering FC Porto to two national league titles in 1997 and 1998.
It was his success there that prompted the Portuguese FA (FPF) to appoint him again as Portugal boss in August 2000 ahead of another former national team coach Carlos Queiroz.
The FPF's decision has been rewarded with Portugal's first appearance in the World Cup for 16