Where and when: SCG, Friday May 10, 7.50pm AEST
Last time they met: Marvel Stadium, round 19, 2018: Essendon 15.19 (109) defeated Sydney 10.6 (66)
The home side overcame some poor finishing to run away with the game thanks to four unanswered goals in the last term. Key defender Michael Hurley's shutdown job on Sydney superstar Lance Franklin earned him three Brownlow medal votes, while captain Dyson Heppell was superb with 31 possessions.
What it means for Sydney: The season. With just one win from their first seven games the Swans are bottom of the ladder, but incredibly, the close nature of the competition leaves them just three wins off fifth spot. This is their last chance.
What it means for Essendon: The Bombers' three wins have come against Melbourne, Brisbane and North Melbourne, but they've faltered against the Giants, St Kilda, Collingwood and Geelong. If they are to be finals contenders, they can't lose to the cellar dwellers.
How Sydney wins: The Swans defence has been under enormous pressure this season, so the midfield must make a stand and get its hands on the footy against Essendon. Josh Kennedy, Luke Parker, Zak Jones and Isaac Heeney have to give the side control of the game.
How Essendon wins: If the Bombers can get enough forward entries, Joe Daniher and Jake Stringer will prove a handful. They're both dynamic athletes and can give the undermanned Sydney defence plenty of problems.
The stat: The Swans gave up 77 inside-50s against Brisbane last week and only lost by 22 points. If they allow the Bombers that many chances on Friday night, it will be a rout at the SCG.
The match-up: George Hewett v Dylan Shiel
The Swans stopper is familiar with the former Giants midfielder and could get the job of trying to curtail his explosive talents on Friday night. Leg speed can hurt Sydney through the middle of the ground and Shiel has burnt them before.
It's a big week for: Joe Daniher
The star forward couldn't back up his Anzac Day exploits and managed just one goal from four kicks against Geelong last week. With Dane Rampe his likely opponent it will be a tough night for the Bomber, but if he can break free he could be a matchwinner.
Big call: Hewett will put the clamps on Shiel and not only hold him under 25 possessions for the first time this year, the Essendon star won't manage more than 20.