A 10-man Broadmeadow went down fighting in a 4-2 loss to 2022 finalists Sydney United 58 in their round of 32 clash at Magic Park on Friday night.
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Broadmeadow came back twice to go to the break at 2-2 after a dramatic opening half which went for more than 70 minutes because of an injury to United's Ante Bakmaz and featured a red card to Magic leading scorer Riley Smith in the 40th minute.
Magic had two shots blocked in an encouraging start before Bakmaz went down 15 minutes in after an aerial challenge with Smith, who received a yellow card.
Play was delayed for 25 minutes as Bakmaz lay prone on the pitch before paramedics took him away on a spine board stretcher and a neck brace. He was knocked out in the incident and experienced pins and needles in one arm. He was taken to hospital but was messaging teammates after the match.
United went ahead nine minutes after play resumed with a penalty from Patrick Antelmi following a handball call against James Cresnar off a cross from Taisei Kaneko.
Magic, though, hit back two minutes later when Jayden Stewardson knocked in a rebound after Danijel Nizic failed to handle a shot from Smith.
The visitors were in front again in the 35th minute when skipper Adrian Vlastelica slid in at close range to score off a Yianni Perkatis nod-on off a corner.
The game was turned on its head in the 40th minute with Smith was given a second yellow, this time for a loose arm hitting Vlastelica in an aerial battle. Replays showed the contact was around the collar.
Magic revived their hopes with an equaliser in stoppage time from Bailey Wells, who flicked on a ball back in from Keanu Moore at a free kick.
Both sides had chances early in the second half. Magic's Uruguayan keeper saved a shot from Antelmi at close range in the 49th minute before the striker was wide with a free header.
Cresnar had a free kick knocked wide in the 51st before calls for a penalty at the ensuing corner and goalmouth scramble were denied.
United broke through in the 54th minute in deflating fashion for Magic. Devante Clut hit a scuffed shot from outside the penalty area and Serpa dived over it.
Will Ingram went close to a leveller for Magic on 69 minutes, hitting the post off a cross from Wells.
Serpa kept Magic in the contest with a full-stretch diving save to deny a cracking strike from Yianni Fragogiannis in the 72nd.
Englishman Ben Diamond had a great chance to send the game to extra-time in the 89th minute but he was wide with his free header.
United put the result beyond doubt four minutes into stoppage time when Alessandro Lacalandra scored on a breakaway counterattack.
Broadmeadow skipper Jeremy Wilson, who battled an ankle injury to get through almost 70 minutes, "was super proud of his side".
"We put in a super effort and I think we were the best team coming out of the first half," Wilson said.
"I think if we kept 11 players on the pitch, I reckon we had them covered, but it just wasn't our night.
"We kept coming back, and it's credit to the boys. Their attitude was perfect tonight. We went down twice, came back twice, and we were trying to fight back at the end, even with 10 men, and we had players coming off the pitch trying to manage minutes and we were still creating chances."
Sydney United supporters threw flares onto the pitch after their goals, while Broadmdeadow fans pushed down a section of fence on the eastern side of the ground when celebrating one of theirs.