The 51-year-old has now been at the helm for 152 games - five with the now defunct New Zealand Knights - and tonight's game against the Victory in Melbourne provided a perfect snapshot of his five years in charge.
There were high, lows, frustrations and periods of promise. Ultimately, however, it ended in disappointment and the Phoenix have now won only one of their last six matches.
For a team who started the season with aspirations of finishing in the top two, they would probably be happy enough now to make the top-six playoffs. It's always been a battle at the Phoenix since their inception and that doesn't look like changing.
When Herbert turned up at Wellington in 2007, he tried to build a club. These days he's trying to build a football team capable of playing attractive, and winning, football. It's what owner Gareth Morgan wants but it's not in their DNA. Not yet, anyway.
Wellington looked good for long periods in the first half tonight and gave as good as they got from Melbourne. They moved the ball around well, were organised at the back and found traction attacking down the flanks through the likes of Benjamin Totori.
But they needed more quality in the final third and playing well in patches is not really enough against a side like the Victory, who started the match in fourth on the A-League ladder. The home side started to gain the upper hand towards the end of the first 45 minutes and looked dangerous on the counter-attack.
That danger became real when Marcos Flores gave them the lead two minutes before halftime when he coolly slotted from a Marco Rojas cross from the left.
Wellington were perhaps a little unlucky to be trailing at the break but that's their lot at the moment. Apart from their season-opening 2-0 defeat of Sydney and 3-0 win over Newcastle in November, they haven't controlled matches and they can't expect to collect points without building pressure.
They often make life difficult for themselves and Flores' strike was the sixth straight game the Phoenix had conceded the first goal. Ominously, Melbourne had also won all five games when leading at halftime.
Wellington's chances of turning that around became almost impossible when former Phoenix winger Marco Rojas tapped in from a rebound off the upright in the 52nd minute.
Rojas has been in sparkling form of late, which must be galling for Wellington fans. Imagine where the club might now be if they had also hung on to Shane Smeltz and Kosta Barbarouses.
Melbourne could have extended their lead as they searched for a third to kill the game off. Mark Milligan, Archie Thompson and Adama Traore all came agonisingly close as Wellington's self-belief and spark ebbed away. The game meandered through the final 30 minutes, although debutant Cameron Lindsay forced a rare sharp save from goalkeeper Nathan Coe.
Herbert's contract is up at the end of the season but he has been guaranteed a job at the club for the next two years. Whether that's as coach and he adds to his A-League record or a director of football will probably depend on what happens between now and the end of March.
Melbourne Victory 2 (Flores 43, Rojas 52) Wellington 0. HT: 1-0.
