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The Staples Wreckers and Darien Blue Wave boys soccer teams have played 180 minutes in two games this season without determining a winner.

In the end the difference between the two FCIAC foes was one penalty kick.

Staples survived by the slimmest of margins and will advance after defeating Darien 5-4 in PKs in the first round of the CIAC Class LL tournament Tuesday at Wakeman Field in Westport.

Each team scored once during the second half of regulation and the game ended in a 1-1 tie after 100 minutes.

“I hate to win by PKs and I hate even worse to lose by it,” Staples head coach Dan Woog said. “It’s a tough way to go. You feel bad. It’s a team game and it comes down to individuals. I’m focusing on the fact that we had a great comeback, we put pressure on them, forced them to their limits and that’s what I’m really pleased with.”

“PKs are what they are,” Darien head coach Jon Bradley said. “Someone’s going to win, someone’s going to lose. I can’t ask for anything more of them. I’m proud of the way they played and I don’t think either team could’ve given any more today.”

No. 10 Staples (12-3-4) will now go on the road to take on the No. 7 Cheshire Rams (11-2-3) in the Class LL second round at 2 p.m., Thursday. Cheshire edged EO Smith 2-1 in overtime on Tuesday.

The Wave (7-5-5) and Wreckers engaged in a physical battle, which was basically a continuation of their regular-season clash that ended in a scoreless tie.

“Darien is a quality team,” Woog said. “They’re well-coached and we have a great rivalry with them. We love playing against them and they bring out the best in us and hopefully vice-versa.”

The Wave had a slight advantage early, testing the Staples’ defense which featured goalie Ry Cohen (5 saves) and backs Nick Ambrose, Gabe Baltierra and Patricio Perez Elorza.

In the last 20 minutes of the first half, the Wreckers turned the tide and generated more offense.

Darien’s defense, which starred Cole Branca, Liam Flaherty, Matt Freeman, Will Henry Harmon, Charlie Sears and goalie Aaron Sears (7 saves), played well and kept it scoreless.

“I thought at the end of the first half, and end of the second half, they had the better of it,” Bradley said. “We had a couple of injuries but the players who came off the bench stepped up well. Especially towards the end of the second half they wore us down a little bit, and then in overtime, it was just two teams being tired.”

The Wave drew first blood less than two minutes into the second half when Connor Olson carried the ball into the right corner and sent a cross in front of the goal. Charlie Sears crashed through the box and drilled a shot past Cohen to put the Wave in front 1-0.

“You only had to watch this game today to realize how much of a good player he is. It was a great finish,” Bradley said of Sears.

The Wreckers drew even in the 63rd minute. Perez Elorza fed the ball to Vaughan Sealey in the midfield and Sealey sent a long ball ahead to Mauricio Inglada. Inglada got his foot on it for a shot around the keeper, who ventured far out from the goal.

“Vaughan gave me a long ball, I saw the keeper coming out, so I just tapped it into the goal,” Inglada said. “I wasn’t sure if it was going in at first, but it did.”

Staples’ attack was relentless down the stretch, but Darien’s defense held on for the tie, forcing overtime. Neither team had any great chances in two 10-minute OT sessions, putting the game in PKs.

Unlike their FCIAC semifinal loss to Trumbull, in which they lost on PKs 3-1, the Wreckers were on the mark this time, as Surya Balaji, Austin Sholes, Nick DiMasi, Eleftherios Pendarakis and Rob Diorio all scored.

The Wave had successful PKs from Charlie Sears, Max Marcin, Will Henry Harmon and Olson, but the game ended when Pedro Calmon-Coelho put his shot over the top of the net.

“We felt we did not take good PKs against Trumbull because we did not take them with confidence,” Woog said. “We trained PKs and the kids went out and hit them with confidence.”

While Staples moves on, the Wave has wrapped up another impressive season.

“We’re in a unique area where people judge you on championships,” Bradley said. “At the end of the day, these boys game out and in 17 games only lost four in arguably the top two divisions in the state (FCIAC and Class LL). And they came out and lost on PKs, so there’s nothing more to say. I’m proud of them. We’ll regroup and get ready for next year.”