The magic of the cup is well and truly alive as Oakleigh pulled off a remarkable upset, eliminating defending champions Sydney FC to qualify for the Round of 16 of the Australia Cup.

The Hellenic outfit downed the Sky Blues 3-1 in their Round of 32 clash at The Home of the Matildas ground on Tuesday evening, delivering the first major upset of this year’s Cup in the process.

The Sky Blues fielded an under-strength side with numerous youngsters for the fixture, owing to injuries as well as the club being in the midst of a squad revamp, and it did not take the Cannons long to capitalise.

The hosts pulled ahead 14 minutes into the contest with a headed goal from midfielder Kingsley Sinclair.

The Sydneysiders were awarded a penalty soon after which new recruit Anas Ouahim stepped up to take, with his first effort being saved by goalkeeper Nick Feely.

Feely stepped off his line, however, and so the penalty was retaken with Ouahim this time slotting it in (25′).

Oakleigh managed to regain the lead before the break via forward Asad Kasumovic, who struck the ball nicely past goalkeeper Andrew Redmayne’s near post in the bottom right corner (38′).

The Cannons then doubled their advantage after a lovely goal from midfielder Emlyn Wellsmore, which saw him finish the ball from the edge of the box into the bottom left (74′).

The result marks Oakleigh’s second victory over the Sky Blues in three years, having previously beaten them in the quarter-finals of the 2022 Australia Cup.

It also makes them just the second team to knock out Sydney FC on multiple occasions (the other being Adelaide United who have done it three times).

The Cannons have set the tone for their fellow Hellenic clubs with South Melbourne and Heidelberg United both striving to match their result in their matches against Wellington Phoenix and Central Coast Mariners respectively.

Olympic FC, the other Greek side in the Round of 32, also have a tough clash ahead as they take on APIA Leichhardt.

All three games will take place next week with Hellas playing on Tuesday 6 August and “Alexandros” and Olympic FC competing the next day.