Orlando City appeared to have an easy path to the knockout rounds entering its match against Atletico San Luis at Inter&Co Stadium in the final match of Group East 2 play in Leagues Cup. But a first-half red card while the game was still scoreless raised the degree of difficulty.

However, Ramiro Enrique’s late first-half goal and heroic defending for the final 45 minutes allowed the Lions (1-0-1, 5 points) to draw San Luis (0-1-1, 1 point) 1-1 and top the group. A 71st-minute goal by Rodrigo Dourado spoiled the clean sheet and the victory in one fell swoop, but the Lions got the last word by knocking the Liga MX side out of the competition with the draw and then winning the penalty shootout, 5-4, to claim the extra point.

“It was an excellent effort from our players,” Orlando City Head Coach Oscar Pareja said after the match. “We want to recognize that heart and that willingness to do the right things is what identifies Orlando City, especially in the period that we have shared here with the fans in these four years. We have players who give everything up, and today was no exception.”

Pareja’s lineup was virtually unchanged from the side that spanked CF Montreal 4-1 nine days ago. The only swap was Ivan Angulo replacing Nico Lodeiro after serving his suspension for a red card in last year’s competition. Pedro Gallese took his usual spot in goal behind a back line of Kyle Smith, Robin Jansson, David Brekalo, and Dagur Dan Thorhallsson. Cesar Araujo and Wilder Cartagena started in central midfield behind an attacking line of Angulo, Martin Ojeda, and Facundo Torres with Enrique up top.

Orlando City started the match brightly, getting forward with a lot of energy and flying around the San Luis penalty area. Cartagena took the game’s first shot in the second minute, driving an attempt from distance that took a deflection but gave San Luis goalkeeper Andres Sanchez no trouble. Two minutes later, Torres won the game’s first corner and the cross found Brekalo in front, but the Slovenian headed it just wide of the left post.

In the fifth minute, Enrique did well to dispossess San Luis defender Julio Dominguez in the penalty area, turning the visitors over. Torres picked up the loose ball and fired from the right but just missed wide of the left post.

San Luis got its first shot in the 14th minute and it nearly resulted in a goal. Vitinho sent a blast from the top of the area on target and Gallese made a diving save to keep it out. The visitors did nothing with the ensuing corner and Orlando cleared the danger. That first attack allowed the Liga MX side to settle into the game.

Cartagena was called for a foul in the 19th minute about 30 yards out from his own goal on the San Luis attacking right. The visitors took the free kick short to the middle and Oscar Macias fired from long range but the shot was always going over the bar.

The game turned in San Luis’ favor in the 27th minute when a turnover in Orlando’s attacking third resulted in Vitinho getting behind the defense in transition. Smith caught up to him just outside his own penalty area and committed the foul. Although he was initially given a yellow card, a quick check of the video led referee Mario Escobar to change the call. Smith was sent off for denial of a goal-scoring opportunity and Orlando City was down to 10 men.

Juan Manuel Sanabria hit the ensuing free kick into the wall. It came back to him and he fired again. This time the shot took a deflection off an Orlando player and went out for a corner. Before it did, Gallese tried to keep it from crossing the line, taking a chunk out of the wet turf and going down hard. After receiving treatment, he was able to continue.

Rather than make a substitution in the first half, Pareja redeployed his troops, moving Cartagena to center back between Jansson and Brekalo, and pushing Angulo into a left wingback role opposite Thorhallsson on the right.

“It is very relevant for us to have players with that versatility,” Pareja said. “Wilder has had a tremendous impact in the way we bounce back from from our slow start. Today was another night where he adapted to the needs of the team and he dropped to that position where he can give us that function as a center back, but at the same time with the intelligence that the position needs to be a midfielder also.”

The Lions did a good job of holding possession for a spell after the free kick and even won a couple of set pieces from distance but couldn’t do much with them.

Jansson gifted San Luis an opportunity with a misplaced backheel pass attempt in his own half in the 45th minute. The wayward pass turned the ball over and Mateo Klimowicz fired a blast from outside the box. Gallese got down and made the save. He bobbled the ball momentarily but none of the visitors were anywhere near him, so he was able to gather it up.

The Lions struck at the death of the first half. Orlando broke in transition with a series of quick passes. Araujo sent the ball forward to Enrique in the middle, and he in turn sent Ojeda up the left side. Ojeda sent in a gorgeous cross to Torres at the back post. A bit too wide to make an attempt on goal, Torres smartly headed it down, back across the box. Enrique ran onto it and slotted it past Sanchez to give the Lions the lead in the sixth minute of first-half stoppage. It was the Argentine’s sixth consecutive match with a goal across all competitions, breaking Daryl Dike’s club record of five.

Ramiro Enrique! @OrlandoCitySC take the lead just before the break!

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Seconds later, the half was over.

Despite being a man down for a good chunk of the first half, Orlando City held the halftime advantage in possession (57.5%-42.5%), corners (3-2), and passing accuracy (86.8%-81.8%). Both teams attempted five shots and both put two attempts on target.

Rodrigo Schlegel replaced Jansson to start the second half, as the captain was on a yellow card.

San Luis started the second half with a lot more possession, looking to pull Orlando’s defense apart. Orlando was able to get forward a few times as well, but both teams struggled to create clear chances in the opening minutes of the second period.

The first good look came the visitors’ way in the 53rd minute. A ball into the area was headed on goal by Yan Phillipe but Gallese was able to stop the powerful attempt. Six minutes later, a shot from outside the box sailed over Gallese’s crossbar.

Second-half sub Franck Boli fired just wide of the left post under pressure from Araujo on the shot.

The Lions finally got a look at goal in the 64th minute off a corner kick. Ojeda’s cross picked out Cartagena but the Peruvian’s shot fizzed just inches over the bar and onto the roof of the net.

Orlando were THIS close to doubling their lead. 😱

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— Leagues Cup (@LeaguesCup) August 5, 2024

San Luis’ relentless pressure continued. Sanabria smashed a shot toward goal in the 65the minute, but Gallese made a diving save to his right to keep it out. A minute later, Benjamin Galdames made a nice play to cut inside on the attacking left and fired from a tight angle. Gallese had his near post covered and the shot banged off the top of the crossbar.

Perhaps Gallese’s best save came in the 69th minute on an absolute cannon blast by Vitinho from the right. The Peruvian made a diving save to knock it off the post at the last second.

However, the San Luis goal that always seemed likely finally came in the 71st minute. The visitors had been working the Orlando City defense side to side relentlessly and it finally paid off with a ball into the box that Dourado was able to head past Gallese to tie the game.

San Luis won a parade of corner kicks down the stretch of the game, and Orlando defended in numbers. Dourado sent another headed attempt wide in the 75th minute.

After surviving several San Luis corner kicks, Angulo made a fantastic play to get out of a crowd of players along the right sideline with the ball, jump-starting the break. The ball ended up on the left with second-half sub Rafael Santos, who smashed a shot that deflected out for a corner. Schlegel got his head to the cross on the set piece but sent his shot wide of the left post in the 88th minute.

From there, Orlando saw out the final seconds of normal time and four minutes of stoppage time to secure the draw and clinch first place in the group.

The strong second half while up a man allowed San Luis to finish with the advantage in possession (54%-46%), shots (23-9), shots on target (6-2), corners (10-5), and passing accuracy (87.5%-85.6%).

Because Leagues Cup matches go to shootouts after draws, the teams went to the penalty spot to determine which side got the extra point, despite it having no impact on the standings. Orlando would have finished first regardless of the outcome, and San Luis could not catch second-place CF Montreal with the extra point.

Vitinho shot first for the visitors, and even though his shot hit the crossbar, it caught the underside and bounced down past the line to give San Luis the advantage after one shooter. Lodeiro answered and the teams swapped successful penalties in the second and third rounds. Sebastien Salles-Lamonge and Cristiano Piccini hit perfect penalties for San Luis, despite Gallese guessing the correct direction both times.

Duncan McGuire, who had come on for Enrique late in the second half — just hours after landing in Orlando from participating in the Olympics in France — and Wilder Cartagena scored to make it 3-3 after three rounds.

The fourth round proved to be decisive. Leo Bonatini hit his shot toward the left post, but Gallese again guessed correctly, and this time he was able to palm the shot away before it could cross the line.

“For us, a lot of the studying that we would do during the week on penalties just wasn’t there for us,” Gallese said. “We thought that they would only really have two guys that have taken for them historically, and the other ones, it wasn’t what I was able to study. It was just kind of what I felt on the direction they would go.”

“Important for us to have Pedro back in his level,” Pareja said.

Rafael Santos buried his penalty to send it to the fifth round with his team leading, 4-3. Franck Boli connected to put the pressure on Orlando’s fifth shooter, who was Thorhallsson. The Icelandic fullback ran up quickly and hit his shot hard. Second-half San Luis goalkeeper Cesar Lopez got a hand to the shot but couldn’t keep it out, deflecting it into the roof of the net from below, giving the Lions the win.

“For us it was important to win it in front of our fans,” Pareja said of the shootout. “For us it was important to keep this momentum. Now we’re preparing for the next one.”

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The Lions will next host another Liga MX side — Cruz Azul, the second-place side in Group East 4 — on Friday at a time to be announced.