This season three Phoenix wins over Vitezslav Lavicka's Sky Blues included 4-2 and 2-1 at tonight's venue.
That second win featured Tim Brown's long-range looper which stunned Reddy.
For Brown, defeat tonight would spell the end of his soccer career following his shock retirement announcement earlier this week. His professional days will end at the same time as the Phoenix' season.
Going into the match with back-to-back losses fresh in their minds may be less than ideal preparation, but striker Chris Greenacre is backing his teammates to banish the losses and, in the process, banish the Sydneysiders.
"It's probably made us a little bit more determined and a bit more hungry," he said.
"Training's been quite feisty this week, which is always good. There's been one or two tackles flying in and one or two arguments. You can tell that the boys are really getting focused and fired up."
While the Phoenix have been assured of a place in the top six for some time, Sydney had to fight through recent weeks, not sealing their place until the last day of the regular season with a 3-2 win over the Newcastle Jets.
The Phoenix have gone more than a month without a win, a 2-0 victory over Gold Coast.
Both coaches are likely to put out the same teams who ended the regular season, with Herbert having few options in sticking with what has been a well-tried line-up.
With an extra player allowed on the bench, Daniel is set to return at least that far tonight after being sidelined with injury.
Key strikers Joel Chianese and Paul Ifill hold the key to their respective team's chances.
Ifill, the cagey veteran, has not been a 90-minute player for 27 matches in the regular season, but has an inherent ability to turn in a magical moment or two on which a game can turn.
Chianese, at 22, is 10 years younger than Ifill and has become the talk of Sydney.
He has been a major influence in Sydney's late rally impressing Lavicka sufficiently to keep two-time league winner Mark Bridge on the bench.
But to be effective, Chianese and strike partner Bruno Cazarine will have to outplay the Phoenix central defensive pairing of captain Andrew Durante and the club's player of the year [again] contender Ben Sigmund.
While the Phoenix begin their finals campaign with the least goals scored (34) of the six contenders, only the top two teams, Central Coast and Brisbane Roar, have a better defensive record.
It promises to be a tense battle, but with Brown's impending departure and given the massive support they will enjoy, the Phoenix might just come away a goal to the good and keep their campaign bubbling along.