Ripon shot 9 for 25 on free throws and missed 10 of 12 attempts down the stretch in a heartbreaking 66-65 loss at Livingston on Wednesday.

The Wolves (8-10) trailed by seven with 1:20 remaining and won it in dramatic fashion, as Harman Singh converted a buzzer-beating put-back layup off a missed 3-pointer.

Making matters worse for the Indians (9-8), senior guard Mario Roach sprained an ankle in the final minutes and is questionable for the team’s Trans-Valley League opener against Hughson on Friday.

“It’s a learning experience for a very young group,” Ripon coach Rod Wright said. “They are learning to close out games and we have to make free throws to do that. With Mario out we had no seniors on the floor down the stretch; it was all juniors and sophomores at that point.”

Ripon outscored Livingston 21-8 in the third for a 54-45 lead. Cody Haines made one of two free throws to give Ripon its final advantage at 65-64 with 11 left.

Cole Stevens and Roach scored 17 points apiece to pace Ripon. Aaron Paschini contributed 14. Anthony Deol registered 17 for Livingston and Singh finished with 13. Blake Jantz (four 3s, 12 points) and Josh Penrod (11 points) joined them in double figures.