The Sky Blues were the only side the Phoenix didn't beat last season, losing twice and drawing the other meeting between the two.
But head coach Ufuk Talay - who joined Wellington from Sydney FC at the start of last season - is undaunted by that record.
"Last season we played our best games against Sydney," Talay said.
"We play a very similar style. We let them go a couple of times when we had them by the throat.
"Sydney are a very settled squad - they've had the same squad for quite a while - but it's a great occasion to play the champions in the first game.
"The boys will definitely be up for it. We're very excited and can't wait to start."
Covid-19 has forced the Phoenix to relocate to Wollongong, 90km south of Sydney, and while there's hope they may play some games in New Zealand if a transtasman travel bubble opens, plans are in place to stay in Australia until June.
But in a marked change from last season, where the side also lived across the Tasman to complete their campaign, the players and coaching staff have sourced their own accommodation as they try to create as much normality as possible. Several have their wives or partners with them, with the likes of David Ball and Luke DeVere shifting their families to Wollongong.
On the field, Talay has had to deal with the departures of a quartet of key players from last season with defenders Libby Cacace and Steven Taylor, midfielder Matti Steinmann and striker Gary Hooper all gone, along with utilities Callan Elliot and Callum McCowatt.
The Phoenix mentor has proven himself to be a canny recruiter though, and has brought seasoned Israeli striker Tomer Hemed and age-group Australian international Josh Laws to the club, along with Kiwi Clayton Lewis and young attacker Mirza Muratovic. James McGarry and Matthew Ridenton also return for a second spell.
Some of the standouts from last season in All Whites goalkeeper Stefan Marinovic, dependable defender DeVere, combative midfielder Cam Devlin, Mexican star Ulises Davila and workhorse English attacker Ball are all back.
One area where Talay wants to see improvement is in front of goal, with Wellington scoring just 38 goals in 27 games last season.
"We created a lot of scoring opportunities last season," noted Talay.
"If we can be more clinical this season - whether that's against Sydney or any other team - we'll be headed in the right direction."
Talay's tenure as Phoenix coach could hardly have started in worse fashion, with Wellington losing their first four matches last season. But a nine-game unbeaten run, and a stretch of 16 matches during which they lost just twice, propelled the Phoenix to third on the ladder before Covid hit. Wellington were being talked about as title contenders, but failed to recapture that form when the season resumed and dipped out in week one of the finals.
"Pre-season has been good, playing some A-League opponents," said Talay.
"Also, not having to start from scratch has been very important to us, building on what we achieved last season.
"Having the core of the group has helped to continue the work we did last season and the new players have settled in very quickly.
"They're new faces but they've played alongside each other in the All Whites."
