Summer signings Gruev and Glen Kamara were both handed starts for Bulgaria and Finland respectively but Finland suffered a 1-0 defeat at home to Denmark while Bulgaria’s clash in Montenegro ended in a last-gasp 2-1 defeat.
Kamara had been named on the Finland bench for Thursday’s Euros qualifier in Kazakhstan in which he came on with 23 minutes left and played a big part in the only goal of the game.
Three days later, United’s summer signing from Rangers lined up as a left-sided centre midfielder against Denmark meaning that he was often looked in combat with departed Whites loanee Rasmus Kristensen who took up his usual right back berth for the Danes.
With the score still goalless, Finland boss Markku Kanerva made a triple change two minutes after the hour mark which included the withdrawal of Teemu Pukki but Kamara stayed on the pitch.
Another change followed with six minutes left as Robert Taylor replaced Benjamin Kallman but Denmark went ahead two minutes later through a fantastic strike from Tottenham’s Pierre-Emile Hojbjerg who found the bottom left corner with a low strike from 25 yards out. His strike proved the only goal of the game, sealing a victory which took Denmark top of Group F in leapfrogging Finland who drop to second.
Gruev, meanwhile, continued his run of starts for Bulgaria who faced a Euros qualifier in Montenegro but a heart-breaking last-gasp 2-1 defeat left them bottom of the group.
Gruev lined up in centre midfield but his side fell behind in first-half stoppage time as Stefan Savic struck for the hosts. Montenegro were then reduced to ten men in the 59th minute when Igor Vujacic was given his marching orders for a second booking and Bulgaria were awarded a penalty. Kiril Despodov saw his spot kick saved but Bulgaria eventually equalised with 11 minutes left through a Preslav Borukov header.
The visitors then looked to make their extra man advantage count but Montenegro provided one last sting in the tail as Stevan Jovetic netted a 96th-minute winner.