Herbert was part of the All Whites team that needed to beat Saudi Arabia by a big margin to keep their World Cup dream alive and they returned from Riyadh in 1981 with a scarcely believable 5-0 win that sent them into a playoff with China in Singapore.
Next month he will return to Riyadh with the All Whites for a four-team tournament. They will take on the hosts on September 6 and, depending on results, either Trinidad and Tobago or the United Arab Emirates four days later.
There are still a couple of vacancies in the All Whites side ahead of their high-stakes home-and-away playoff against the fourth-best nation from North and Central America for a place at next year's World Cup and Herbert is hoping the picture becomes a little clearer during these two games.
One is in central midfield and the other is whether he can find a right-back proficient enough for him to contemplate a back four.
The All Whites coach sprang a couple of surprises in his 18-man squad to travel to Saudi Arabia, with recalls for Finland-based duo Chris James and Kris Bright and a call-up for Waitakere's Jake Butler. In the words of Herbert, they were selections that were "worth a shot".
"If we find a piece of the jigsaw that helps us, great," he said. "If we don't do that, I'm not going to know.
"There's a little bit of look-and-see with these two games. In the end we might come back and say, 'no, we're not comfortable [with these players], but I don't want to miss the opportunity of not having a look."
The main ones Herbert wants to peruse are James and Butler. He hasn't found an adequate holding midfielder since Tim Brown retired last year.
James, who was seen as a considerable talent in his youth when at Fulham and who last featured for the All Whites at the 2009 Confederations Cup, has been playing as a holding midfielder with his Finnish club.
Herbert also wants to see if Butler can make the step up after appearing for New Zealand A against Jordan in June.
Ivan Vicelich, Andrew Durante and Tim Payne remain as options to partner Michael McGlinchey in midfield for November's playoffs.
The other conundrum is at right-back, a position this country has struggled to fill for more than a decade and which prompted the switch to a 3-4-3 formation for the 2009 playoffs against Bahrain.
Ben Sigmund has played there a handful of times before but Herbert is unconvinced the Phoenix defender would be able to cope against quick wingers. Louis Fenton might also come into the equation if he can impress when the Phoenix kick off their new A-League season - new Wellington coach Ernie Merrick plans to convert Fenton from a winger to a fullback.
"I think it's early for him but, if he can prosper over the next few weeks, it's a possibility," Herbert said. "We could try him in the October window."
The likelihood is the two games in October will both be away - they had originally hoped to play one in Central America and the other in New Zealand four days later to replicate what they will face in November.
