Facing each other in a second successive Euros qualifying campaign, both nations will be hoping to put past troubles behind them after finishing as the bottom two sides in their last crack at reaching the finals.
To begin with the hosts were made to wrestle for control, and when they eventually managed to, they should have gone ahead.
Stefan Savic’s slip at a crucial moment allowed a two-on-one scenario, where many expected Kiril Despodov to go for goal. Instead, he fed teammate Ilia Gruev, whose tame near-post shot was saved by Milan Mijatovic.
Interestingly, in an attempt to make up for his error, Savic also hacked down Gruev following his shot, and despite a VAR check, no penalty was awarded.
As the first half reached its climax, it was the Brave Falcons’ turn to pile the pressure on. They entered the match with the additional motivation of reaching their first tournament finals since becoming an independent country, though their push for the opener was stopped by a defiant Daniel Naumov.
The Bulgarian goalkeeper made three fantastic saves, first denying Savic by clawing his header off the line following a corner, then rushing out of his goal to smother Adam Marusic’s later attempt when through on goal.
Deep into time added on, Naumov finally produced a fantastic diving save to divert Vukan Savicevic’s shot from heading into the top corner.
This inability to find the back of the net created the growing sense yet another draw betwen the sides was on the cards, following on from the two stalemates that took place in Euro 2020 qualifying.
Desperation was growing inside the Huvepharma Arena for Bulgaria to take a grip on proceedings, and manager Mladen Krstajic echoed these cries with his four-game unbeaten record since taking the Lions job on the line.
They failed to do so, leading to Montenegro snatching the lead with 20 minutes to play through Krstovic’s first international goal - an easy tap-in into an empty net after Vladimir Jovovic’s neat build-up play.
Whilst nerves were no doubt present as they headed towards only their second victory in eight matches, there was also some solace for Montenegro as each of their last eight games on the road have seen only the winning side get on the scoresheet.
The home side pushed to rescue a draw deep into stoppage time, but in the end the Montenegrans held out for an important three points, thanks in-part to Savic’s 90th-minute block on the line to deny Georgi Rusev.
Flashscore Man of the Match: Nikola Krstovic (Montenegro)