The Winthrop/Monmouth football season finally gets its postseason started. Oak Hill and Cony would like to keep theirs going.

The bye weeks are done, which means the Ramblers, after earning a pass through the first round of the Class D playoffs following a bye in the final week of the regular season, get to take the field and try to play to their billing as the South region’s No. 1 overall team. They’ll line up against No. 4 Dirigo in a rematch of a Sept. 16 game, one that went down to the wire with W/M needing a touchdown pass in the final minute to eke out a 14-6 victory.

Elsewhere in D South, No. 3 seed and three-time defending champion Oak Hill looks to go back to the regional final in Saturday’s game at No. 2 Lisbon. And in Class B North, No. 6 Cony looks to ride the momentum of a stunning win over No. 3 Lawrence in a tilt against second-seeded Brewer.

There will be some question marks surrounding W/M (7-0) when it takes the field tonight — first and foremost, whether all the rest cast a layer of rust on an operation that was working smoothly throughout the second half of the season.

Coach Dave St. Hilaire, however, doesn’t see that being a concern.

“We looked pretty good at Madison (in a scrimmage) last week,” he said. “That was a great time up there, Wednesday, of getting something. Because if we hadn’t gotten that, we might have had that (rust).”

The matchup could still be a close one. Few teams challenged the Ramblers as well as the Cougars did, as Dirigo held W/M to six points and a tie through 47-plus minutes of play in September. The dam finally broke with 16.3 seconds left, however, when quarterback Matt Ingram hit Bennett Brooks with a 44-yard touchdown pass for the win.

St. Hilaire doesn’t think that was a fluke he saw from the Cougars.

“They’re a tough, physical team. They don’t play a lot of guys, they move some guys around and try to maximize what they bring,” he said. “They gave us everything and more last time. … They’ll have some different subtleties for us, but it’s the same physical team that we faced before.”

The intensity will be there, and part of the challenge for the top seed will be matching it.

“We’ve got to play smart, disciplined,” St. Hilaire said, “and be hellacious with aggressiveness.”

The Ramblers did that more and more as the season went on. W/M looked mortal early in September, but began to hit its stride into and throughout October while leaning on a rushing attack led by Alec Brown and Nate Scott.

“We would have liked to see better execution all the way up through,” St. Hilaire said. “But 7-0, we did what we needed to do and it set us up for the best possible second part of the season, which is now.”

• With the three consecutive titles under their belt, it’s been a while since Oak Hill was an underdog. That’s what’s facing the Raiders, however, when they take on a Lisbon team that won the first matchup between the teams, 36-14.

“We can’t have any mistakes. We can’t turn the ball over, no penalties,” coach Stacen Doucette said. “We’ve got to do our jobs and we’ve got to (perform) our assignments. They’re a physical team, we know that, and we’ve got to limit our mistakes.”

Doucette likes the way the Raiders are coming into the game, however. Oak Hill topped sixth-seeded Traip Academy by a modest 16-8 score, but Doucette liked the way the team competed throughout the rainy contest, weathering the conditions to punch its ticket to the semifinals.

“We thought that was our best two halves of the year together,” he said. “I knew that the weather would be an equalizer, and it kind of was at times, but usually those type games are really hard to win. We were happy just to get out of there with a win.”

The key takeaway from that game was the defense, as Oak Hill allowed only 35 yards of total offense. That unit will be tested against Lisbon, which sports a big line and powerful running back combination of 285-pound Noah Francis and big-play back Jared Glover. And if the Raiders commit too hard to the ground game, quarterback Tyler Halls likes to look deep to wideout Kurtis Bolton.

“I think they’re going to use their size always first, and wait for the correct moment to strike vertically,” Doucette said. “And I think they will.”

The key then is for Oak Hill to get the most out of its possessions, leaning on a backfield led by Steve Gilbert but that also gets contributions from Cruz Poirier, Austin Noble and quarterback Matt Strout.

“We’ve always been a type of coaching staff and program where it’s not about a certain player, it’s about the play,” Doucette said. “We like to keep everybody fresh and healthy. A lot of people work hard in practice, we try to reward all of our players with touches.”

• Cony has shocked Class B once already this postseason. Doing so again against the vaunted Witches, coach B.L. Lippert acknowledged, will be even tougher.

“We have some confidence to finish the season, but that doesn’t mean we can expect to just go in there and have our way,” Lippert said. “They’re a very good football team, they’re 7-1 for a reason. We’ve got to play really, really well up there to have a shot, and that’s what we want to have in the fourth quarter. A chance to pull something off like we did last week.”

Keeping up with the Witches and their powerful ground game will require nearly flawless execution on the Rams’ part.

“You can’t expect to go up there, hang 40 on them and shut them out. We know it’s going to be a battle,” Lippert said. “I think we’ve got to limit three-and-outs. … If our defense is on the field for 10, 12, 15 plays, and then we go three-and-out and they’re right back out there, that’s putting them at a major disadvantage.”

Brewer is big but also athletic, with 6-foot-4, 260-pound Austin Lufkin leading a line that paves the way for 240-pound Trey Wood, who ran for 267 yards and four touchdowns against Cony earlier in the year.

The Cony defense will look to limit the damage this time, but the Rams’ passing offense, led by Taylor Heath and Jordan Roddy, will need to be sharp.

“We’ve got to stay on the field offensively,” Lippert said. “Execute our gameplan, establish some element of a ground game and shorten the game, to an extent.”

Drew Bonifant — 621-5638

[email protected]

Twitter: @dbonifantMTM