But, in coming close to landing his second victory of the season on the over-50s circuit, the Scot has jumped to second behind Bernhard Langer in the Charles Schwab Cup.
Montgomerie, who won the Pacific Lakes Bear Mountain Championship in Canada a month ago, closed with a 70 in breezy and wet conditions at Sherwood Country Club in Thousand Oaks, California, for a 12-under-par 204 total.
However, helped by an eight-foot birdie putt at the 14th, Penrice Jnr finished a shot ahead of the three-time Senior major winner after also signing off with a two-under-par last-day effort.
Montgomerie, who parred the final five holes, described the weather conditions as “just miserable”.
Each dollar earned in the first two events in the new Play-Offs are worth two points. Then, at the third one, the Charles Schwab Championship, points will be reset so that the top five only have to win to capture the Charles Schwab Cup.
Montgomerie improved two spots in the standings and trails leader Bernhard Langer, who withdrew before the start of the first event because of a left knee injury, by 1,038,941 points.
Russell Knox has jumped one spot to 19th in the world rankings after his top-10 finish in the WGC-HSBC Champions in Shanghai.
The 31-year-old has now been 20th or better in the standings since winning the Travelers Championship on the PGA Tour earlier in the year.
As predicted, Rory McIlroy has climbed to second behind Jason Day - the highest the 27-year-old Ulsteman has been since the WGC-Cadillac Championship back in early March.
On the back of his Shanghai success, Japan’s Hideki Matsuyama has jumped five spots to fifth.
After Knox, Martin Laird is the next highest Scot in 138th, having dropped a spot from last week.
Paul Lawrie has bolstered the Scottish contingent in this week’s Turkish Airlines Open to four after securing a late invitation for the first of the European Tour’s three Final Series events this season.
The Aberdonian, who joins Marc Warren, Richie Ramsay and David Drysdale in the field at Regnum Carya in Belek, will be making his first appearance in the event since he played in its inaugural staging in 2013.
The opportunity has been given to him by Chubby Chandler, whose management company, ISM, brokered the deal for the big-money tournament, with Lawrie joining Ryder Cup captain Darren Clarke on the list of invitees.
“I got a text from Chubby last night saying he had got me an invitation, which is great as I really enjoyed the tournament when I played it a few years ago,” said Lawrie.
The 47-year-old ended the regular season by finishing fifth in the Portugal Masters last Sunday and added: “That was really good so hopefully I can keep it going this week.”
Cody Gribble held off fellow Americans Chris Kirk and Luke List as well as Englishman Greg Owen to claim his first PGA Tour title with victory in the Sanderson Farms Championship in Mississippi.
The 26-year-old rookie closed with a seven-under-par 65 at the Country Club of Jackson for a 20-under-par 268 total, finishing four shots ahead of the field.
Gribble, who had started the day a stroke behind playing partners Kirk and List, had two birdies on the front nine before picking up shots at the 11th, 13th, 15th, 16th and 17th as he made a strong finish.
Ross Kellett has vowed to learn from the disqualification that cost him a place in this week’s Challenge Tour Grand Final in Oman.
The Motherwell man signed for an incorrect score in the final round of the Ras Al Khaimah Challenge to finish 48th in the Road to Oman.
“A horrible feeling,” admitted Kellett of missing out on a cheque that would have been enough to get him to the season-ending event. “However, I will learn from it and move on.”
It was sore finish all round for the Scots in the second-tier circuit’s penultimate event of the season at Al Hamra Golf Club.
After getting himself to within a shot of the lead at the turn in the final round, Duncan Stewart started for home with three consecutive double-bogeys and ended up closing with a 75.
That dropped him 19 spots to joint-24th and also saw him slip one place to tenth in the Road to Oman heading into that Grand Final, which starts on Wednesday.
Scott Henry, who closed with a 70 to finish joint-32nd in Ras Al Khaimah, will be the only other Scot in that line-up after David Law’s late bid came up short.
Needing to finish second outright, the Aberdonian signed off with a 72 for a share of 11th. His main goal had been trying to climb into the top 70 on the money-list and secure a full Challenge Tour card again for next season.
However, the two-time Scottish Amateur champion fell agonisingly short as he ended the regular season sitting 72th in the rankings.
“I’m gutted, but I gave it my all this week,” said Law, who, due to Frenchman Romain Langasque having started the season as an amateur, actually came up just one spot short.
Both Kellett and Law now turn their attention to this week’s European Tour Qualfiying School in Spain, where the Scottish hopefuls will also include Grant Forrest.
In his first Challenge Tour event as a professional, the 23-year-old gave a good account of himself in Ras Al Khaimah, finishing joint-32nd after rounds of 67-71-69-72.
Paul Doherty made a great start in the MENA Tour’s Tour Championship in Oman.
The former Scottish Boys’ champion carded a four-under-par 68 at Muscat Hills to sit joint-second, one shot behind English pacesetter Daniel Owen.
“Today’s golf was good,” said Doherty. “I had a wee tip off a good friend of mine on the Tour and managed to strike my irons a lot better to set up a lot of chances.
“I didn’t hole much but hopefully I will tomorrow. The birdies were all pretty close, which is a good sign.”
The top-three on the third-tier circuit’s money-list after the event get into the Dubai Desert Classic as well as spots in the Asian Tour Qualfying School. The top five also get Sunshine Tour cards.
“Those sort if rewards would be massive,” admitted Doherty, who got into this year’s Desert Classic on the European Tour through the same route, “but I believe I need to win for that to happen.”