Both teams are fighting for second spot in the group, with the promotion and relegation places already determined.
Match preview
Having missed out on promotion to League B by two points to Armenia in the last campaign, Macedonia have fallen a little short in Europe's third tier once again.
Considering that they qualified for Euro 2020 - before beating Italy to set up a play-off against Portugal to qualify for the World Cup later this year, which they lost 2-0 - the Lynxes may feel they have proven that they can compete at a higher level.
However, a 2-0 defeat away to Georgia on Friday ended their hopes of doing so, with Napoli sensation Khvicha Kvaratskhelia sealing his nation's victory after Bojan Miovski's 34th-minute own goal had given the visitors an uphill task.
With a one point advantage ahead of third-placed Bulgaria in Group L heading into Monday's meeting in Skopje, head coach Blagoja Milevski will want to ensure that his players do themselves justice and claim second spot by avoiding defeat.
After being relegated from League B in the last campaign, Bulgaria would have had aspirations of an instant return to Europe's second tier.
However, Friday's 5-1 win over Gibraltar was their first victory of this rendition of the Nations League, with five different goalscorers ensuring that they would at least avoid the agony of being relegated to the bottom league in the competition.
Former Maccabi Haifa boss Mladen Krstajic was overseeing his first game in charge since taking over two months ago, and while the lack of quality on display from their opponents must be factored in, it was certainly a positive start following a winless run of seven matches prior to his appointment.
Monday's match at the Philip II Arena will provide a far sterner test of Krstajic's management and his players' abilities, but should they be able to claim a surprise victory on the road, snatching second spot in the group would be a platform to build on for the future.
North Macedonia Nations League form:
D
W
L
W
L
North Macedonia form (all competitions):
L
D
W
L
W
L
Bulgaria Nations League form:
D
L
D
D
W
Bulgaria form (all competitions):
L
D
L
D
D
W
Team News
Stefan Ristovski, Arijan Ademi, Darko Churlinov and Valon Ethemi all pulled out of Macedonia's squad ahead of their trip to Georgia due to injury, and the quartet will not be involved on Monday either.
Aleksandar Trajkovski, who has bagged 20 goals at international level, could come into the attack after only being used from the bench in the 2-0 defeat on Friday.
Bulgaria, meanwhile, could hand international debuts to Ivan Yordanov, Hristiyan Petrov, Mateo Stamatov and Ivan Dyulgerov at some stage of the match.
However, Krstajic is unlikely to make too many changes after such a strong showing in his first game in charge against Gibraltar on Friday, as he looks to make a positive impact at an early stage of his tenure.
North Macedonia possible starting lineup:
Dimitrievski; Todoroski, Velkovski, Musliu, Alioski; Askovski, Bardhi, Spirovski, Elmas; Ristovski, Trajkovski
Bulgaria possible starting lineup:
Naumov; Hristov, Antov, Nedyalkov; Turitsov, Gruev, Krastev, Petkov; Despodov, Stefanov, Kirilov
We say: North Macedonia 1-1 Bulgaria
Bulgaria are heading into this clash with more momentum after their thumping win over Gibraltar in Krstajic's first game in charge on Friday.
However, Macedonia should have enough about them to avoid defeat and hold onto second place in Group L.