Pickering's three wins is more than the last two years combined, but it still wanted to head into the offseason on a high note.
However, the Red Devils could not end the season on a win, falling to Oakdale 26-7 Friday night at home.
"I thought we played pretty well," Pickering head coach Ryan Russo said. "Their running back had a good night, but I thought, for the most part, we bottled him up. At the end of the night, we looked at the stat sheet, and he got his yards. I felt like we had a good game plan on offense, but we struggled a little bit, because all year Oakdale's defense has been good and it was good last night. We wanted a win going out, but it didn't happen. I told them I was proud of them and that we laid the foundation to move forward."
Pickering's offense struggled to get rolling, racking up just 135 total yards.
Oakdale went up 14-0 with a touchdown run and a 30-yard fumble return for a touchdown.
Pickering (3-7, 0-5) got on the board before halftime with a 1-yard touchdown run by quarterback Marlon Freeney.
Oakdale added a touchdown in the third quarter and closed out its win with a score in the fourth quarter.
Seven of the nine Pickering drives were five plays or less, and Oakdale's ground-and-pound offense kept the Red Devils off the field.
"They sold out to stop the run and played really aggressive all night," Russo said. "They forced us to throw the ball more than we wanted to. We just didn't execute on some stuff that we normally do. Hats off to them."
Pickering graduates nine seniors, but Russo hopes to keep building into next season.
"The 2020 season starts Tuesday," he said. "We'll wrap up a few things, but we have to get started. I told the team after the game that we need to have a big offseason. We are going to restructure some things for the winter and into the spring. We're excited about it. I think the kids are excited about it, and we have to look to get some more kids out for some depth. We learned that the hard way. We're ready. You don't want to see the season come to an end in the regular season. You want to make the playoffs, but at the same time, there is some excitement with what we're doing."