A lot of players have come and gone over the past decade, but the duo have stayed faithful and will play their 100th first-class games over the next month.
Utility back Masoe will reach the century on Saturday in Oamaru against Poverty Bay, while two weeks later, prop and captain Darling will reach his on the road against East Coast.
The duo's games had come in both North Otago and New Zealand Heartland XV jerseys, and while both remained humble, they acknowledged the milestone as special.
''I don't really know,'' Darling (31) said when asked how he felt.
''I mean each game is special to me, so to have 100 of them, I don't really know, it feels a bit surreal.''
Meanwhile, the 36-year-old Masoe called it an ''achievement'', although it was one that took a while to sink in.
''It wasn't even until last week that I sat down and thought about it and the more I think about it and the more people talk about it, I realise how special it is,'' he said.
''But it wasn't a big deal at the start.''
The pair had been part of the Meads Cup-winning sides of 2007 and 2010 and both picked out those victories as highlights.
Masoe also mentioned winning two Lochore Cups and eight of the past 11 Citizen Shield titles with Old Boys.
Darling added that Ranfurly Shield challenges against Canterbury and Southland were special.
The duo were good mates and had co-coached and played in the Old Boys team which won the North Otago club competition this year.
They had also played nine games across four seasons together for the New Zealand Heartland XV.
North Otago had experienced a high turnover in players in recent years, but the community was the main reason both players gave for sticking with the team.
''It's quite a tight community in Oamaru. It's not a very big town,'' Darling said.
''So it's nice to see everyone get in behind you and that's why you do it, and also for your family, too.
''It's a nice feeling running out there in front of people that you know.''
Darling was born in Oamaru and attended Waitaki Boys' High School, where he played four years in the first XV.
Having debuted for North Otago in 2007, he had played the majority of his career at loosehead prop, although had spent some time at hooker.
He first captained the side in 2011, and after a break from the leadership role in 2013 and 2014, took it back over in 2015.
An apprentice builder and father of two, he hoped to keep playing as long as he could.
Meanwhile, Masoe had grown up in Samoa, before moving to Dunedin - where he had relatives - to try to help his family. He spent three years in the city, studying, doing odd jobs and playing for Green Island.
In 2007 a friend asked him if he was interested in pulling on the North Otago jersey and he took the opportunity.
A utility back, Masoe predominantly played as a winger in his early years, although had been used more in the midfield in recent times.
Also a father of two - with a third on the way - Masoe works for the North Otago Rugby Union as the Pasifika youth mentor.
