Andrew Yaraghi reached the boys state tennis semifinals three years ago as a freshman, but the road back to the semis for the Friends senior took him down an unexpected path.
"I can confidently say she was the best player I've played so far ," said Yaraghi, 18. "It was just the way she changed direction of the ball, it was better than anybody I had played so far, and the mental aspect made it really difficult, too."
Yaraghi said he had never faced a female opponent in a tournament, and added that the experience was "very weird."
Yaraghi won, 6-1, 6-4, and will play Vihar Shah of Herricks Saturday for a championship berth. Defending state champion and top-seeded Josh Levine of Cold Spring Harbor was the third Nassau singles player to advance to the semis, while Long Beach's top-seeded doubles pair of Ethan Bogard and Matt Barry also reached the semifinals after eliminating Jeremy Schnapp and Alex Ricciuti of Hills East.
Gleason, 17, a senior committed to Notre Dame, had competed with her school's girls team and qualified for the girls state championship for five seasons, finishing third in state in 2010. She said she wanted to compete at a higher level and decided that playing on the boys team would give her that opportunity.
She was declared eligible to compete with the boys by her school district in accordance with state rules that say sports where schools have both a boys and girls team, the state allows for females to "participate on a team organized for males" in order to "meet the needs of the exceptionally talented girl." Males are not afforded the same opportunity.
"For the female exceptional athlete, it must be approved by their superintendent to allow the player to compete in a boys sport," boys state tennis coordinator Selina DeCicco said. "She wanted to challenge herself and the school district and the section stands behind her."
Gleason finished second at the Section V (Rochester/Finger Lakes) boys individual tournament to qualify for states. Against Yaraghi, she led by two breaks in the second set before Yaraghi rallied.
"He is a great player," Gleason said of Yaraghi. "He had a lot of power and was consistent, so I was just going for everything because I knew I was the underdog.
"It was a great experience," she said. "I loved it so much. It's great being here where the U.S. Open is played and it's just great competition . . . It was a tough decision but I'm glad I made it."
In other singles matches, Whitman's Brandon Stone reached the quarterfinals with a 6-0, 6-0 win in the second round but then was eliminated in straight sets. Zain Ali (Hills East) lost his second-round match, 6-4, 6-2.
In doubles, Westhampton's J.D. Sipala and Cooper Lacetera came back from a 2-5 hole in the third set of their second-round match to reach the quarterfinals, but failed to reach the semis after a three-set defeat. North Shore's Austin Davidow and Alex Sacher also reached the quarterfinals and lost in three sets. Both pairs will compete for fourth place on Saturday.
In the consolation bracket, the Syosset pair of Kevin Katz and Ian Baranowski and Suffolk singles champion Jeremy Dubin (Southampton) advanced to the consolation finals by winning three matches Friday.