Georgia or Belarus lie in wait for the victors of this semi-final, meaning at least one of the four teams will make their maiden appearance in the Euros next summer.
North Macedonia are still waiting to make their mark at a major international tournament since becoming independent, but Igor Angelovski's men held their own in the group stage and managed to finish third above Slovenia on head-to-head points.
The Red Lynxes enjoyed two victories over Latvia as well as wins over Slovenia and Israel in Group G - won by Poland with Austria clinching second spot - and North Macedonia can feel confident about their chances of advancing to November's playoff final.
Angelovski's side qualified for the Euro playoffs courtesy of their stellar performance in the 2018-19 Nations League, which saw them finish top of the pile in Group D4 to gain promotion to League C, where the Red Lynxes have made a strong start.
September saw North Macedonia overcome Armenia and draw with Georgia, and Angelovski's men have another fixture against the latter to look forward to in the month of October, with Estonia also waiting to take on North Macedonia three days after their showdown with Kosovo.
Kosovo have certainly made a name for themselves just four years after being accepted as a UEFA member, with Bernard Challandes's side finishing third in qualification Group A behind England and the Czech Republic.
The Dardanians were involved in that unforgettable 5-3 thriller with the Three Lions back last September, and Kosovo picked up victories over Bulgaria, Montenegro and the Czech Republic in their quest for a first ever appearance at the European finals.
Kosovo's 2018-19 Nations League campaign could hardly have gone any better - Challandes witnessed his side top Group D3 to earn promotion to League C and secure a spot in the European playoffs.
However, September proved to be a challenging month for Kosovo as they drew with Moldova before losing to Greece in their first two games of the 2020-21 Nations League, and Challandes's side face another tough opponent in Slovenia this weekend.
Unless Romania are victorious in Path A, the winner of the Path D playoff route will enter Group C in next summer's tournament, which is currently occupied by the Netherlands, Austria and Ukraine.
Otherwise, North Macedonia, Kosovo, Georgia or Belarus face an extremely difficult first tournament in Group F against France, Germany and reigning champions Portugal.
North Macedonia Euro Champ Qualifying form: DWWLLW
North Macedonia form (all competitions): WLLWWD
Kosovo Euro Champ Qualifying form: WWLWLL
Kosovo form (all competitions): WLLLDL
Napoli midfielder Elif Elmas has tested positive for COVID-19 and is not in the North Macedonia squad for the upcoming fixtures, while veteran goalkeeper Martin Bogatinov has also contracted coronavirus.
Leeds United's Ezgjan Alioski could potentially be moved further up the field in order to accommodate the loss of Elmas, although Ferhan Hasani is more likely to fill the void on the left flank after being recalled to the setup.
North Macedonia's record appearance maker and top goalscorer Goran Pandev - still going strong at 37 - is set to spearhead the attack.
As for Kosovo, Werder Bremen's Milot Rashica, who was linked with a move to Aston Villa during the transfer window, is recovering from a knee injury and will play no part in October's fixtures.
Lazio forward Vedat Muriqi had a hand in all three of Kosovo's goals in their eight-goal thriller with England, but the 26-year-old is another high-profile name to miss out here due to injury.
Recent reports have suggested that Amir Rrahmani is another Napoli player to have tested for coronavirus, which would rule him out of Kosovo's matches as well.
North Macedonia possible starting lineup:
Dimitrievski; Ristovski, Musliu, Velkovski, Alioski; Ademi, Spirovski; Trajovski, Bardhi, Hasani; Pandev
Kosovo possible starting lineup:
Muric; Vojvoda, Aliti, Dresevic, Paqarada; Berisha, Shala, Rashkaj; Celina, Nuhiu, Zeneli
We say: North Macedonia 2-1 Kosovo
Both teams have made differing starts to their Nations League campaigns, but those results pale into insignificance when it comes to a playoff semi-final with a spot at the European Championships at stake. That being said, Kosovo will have to make do without a number of their well-known players, so we are backing North Macedonia to prevail and advance to November's Path D playoff final.