But he couldn’t have felt better.

Greenleaf rallied to win the 18th hole and then a playoff hole to advance to the Maine Match Play Championship quarterfinals. He did so by defeating 13-time Maine Amateur champ Mark Plummer on the 19th hole.

“I got 37 holes in today,” Greenleaf said as rain still dripped from his waterlogged hat. “That’s my first win against him. It’s the first time I’ve played against him in match play. I’ve played with him a bunch of times, but it’s the first time in match play. So it’s sweet, and worth all the misery.”

It was a challenging day for golfers in the first two rounds of the tournament at Martindale Country Club. After a morning round in steadily declining conditions, players in the Round of 16 faced steady rain and winds, but the golfers were still able to complete the round.

“It was hard holding onto a club,” said Brian Angis, who also had a significant win, beating defending champion Ricky Jones in the afternoon. “Your back is soaked. Everything is saturated. People weren’t playing well.”

Biddeford-Saco’s Angis and Sable Oaks’ Greenleaf were among eight golfers who advanced to Wednesday’s quarterfinals. Other winners include Martindale’s Andrew Slattery, Maine Amateur champ John Hayes IV, Sam Grindle, Joe Walp, Jeff Cole and Luke Ruffing.

“It’s going to be different,” said Slattery, who is now 5-4 overall in the match play tourney and is advancing to the second day for the first time. “I’ve never seen Wednesday. It’s going to be fun and exciting. I’ll be facing John (Hayes). So that will be tough, but at this point, with only eight guys left, anyone you play is going to be tough. It doesn’t matter who it is, it’s going to be tough no matter what.”

Hayes had the first tee time and played the entire round without inclement weather. Rain came in later, and intensified the rest of the day.

“It was night and day,” Hayes said. “The course was playing very different. Sometimes, I’d be 20 or 30 yards back from where I was in the morning. So I’d have to play completely different.”

Angis managed to get through eight holes before the weather came. He slogged it around the rest of the day.

“I played in the rain all day,” Angis said. “It got windier and it got cold. My back started getting wet. Stuff started sticking. I just thought of it as going out and playing and whatever happens happens. Once you’re wet, you’re wet.”

Greenleaf had already survived a tough match when he beat fellow Sable Oaks golfer Mike Doran in the morning. He and Plummer discussed how brutal conditions were when they teed off in the early afternoon for the Round of 16. The two were even on the back before Plummer took the lead, setting up Greenleaf’s unlikely comeback.

“We were all square through 16, and I chunked one into the pound on 17,” Greenleaf said. “I went one down and got lucky enough to find my ball on 18 and five was good enough.”

Greenleaf won 18 and then won the 19th hole to get the victory. Both holes needed a little good fortune. Greenleaf is now 13-4 overall in the match play tourney. He won the event in 2013 and lost in the final in 2011. He faces another Sable Oaks golfer in Cole, who was a teammate of Greenleaf’s in the Club Team Championship. Cole was the runner-up to Jones last year.

“I got lucky,” Greenleaf said “I’ll be perfectly honest. I had two terrible tee balls on both tees. I found the first one on 18 and five was good enough to win. I hit one left off of #1 and I took a penalty shot, but five was good enough to win there too.”

The last time Greenleaf lost in the Match Play Championships was to Angis, who also took down the defending champion this year in Jones.

“Last year I lost to Ricky in the semifinals,” said Angis, who played with Jones through the first two rounds of the Maine Amateur last month. “I beat Curtis Jordan and Matt Greenleaf. So I’ve beaten the defending champion the last two years. Ricky is a tough player. I’ve played with him a couple of times the last few years. If you can beat him, you can beat anybody.”

Angis and Jones were close early on, but then Angis started to open up a lead. He struggled over the final few holes but managed to secure the win.

“He started 1-up,” said Angis, who plays Ruffing in the quarterfinals. “Then I was 1-up. The real turning point for me was I birdied #7 and #8. I was 1-down and that put me 1-up. Then I won #10, #11 and #13. So I was 4-up through 13.”

Slattery lost in the first round last year and had never gotten past the opening day of the tourney. He beat Peter Wright in the morning and then won an afternoon match against Norway’s Joe Baker. 

“I think I was 3-up at the turn, so I had a decent lead on the back,” Slattery said. “It was nice and wet and deep and the ball wasn’t going anywhere. Everything was soaked. It was tough.”

Even being on his home course didn’t help him as conditions worsened in the afternoon. 

“Even if you know the greens and the shots, you still have to make the putts,” said Slattery, whose pairing with Hayes features the last two Maine Amateur champs. “Knowing the course helps, but you still have to do it. That makes everything different. The cold, the rain and the wind changes everything.”

Hayes was the top seed and beat Mike Caron in the morning. Then he edged Joe Alvarez in the afternoon.

“You couldn’t make nearly as many birdies,” Hayes said of the afternoon round. “I just went for par pretty much. You can make a birdie here or there, but it was mostly just getting pars.”

Hayes had the lead early but made a par on the ninth hole that set the tone for the back.

“I had a 15-footer,” Hayes said of his par putt. “Joe made a great up-and-down. That kept me 3-up. That 3-up going into the back nine was huge because match play can change so fast. It was a huge momentum swing.”

The morning round had only six golfers that beat higher seeds, including Greenleaf. Alvarez was the 17th seed and beat Malcolm Oliver, the 16th seed. Baker was the 24th seed and beat ninth-seeded Greg Martin. Gary Manoogian was the 27th seed and beat sixth-seeded Lowell Watson. Thomas Bean, the 26th seed, beat Neil Lyons, ranked seventh. Ashley Fifield was the 21st seed and beat 12th-seeded Curtis Jordan.

A pair of other Martindale golfers played but lost in the opening round. Will Kannegieser lost to Grindle, and Brian Bilodeau lost to Plummer. Fox Ridge’s Craig Chapman lost to Walp.

The quarterfinals continue Wednesday morning with the semifinal round teeing off around noon. The championship round is scheduled for 7 a.m. Thursday.

kmills@sunjournal.com