Rabotnicki managed to beat Estonian side Trans with 4:1 away in Tallinn and succesfuly started the European campaign.

After 16 minutes Krste Velkoski opened the score, but the Estonians tied on 1:1 just 10 minutes before half-time. In the beginning of the second half, captain Borce Manevski brought a new lead to Rabotnicki. The Estonian team made three substitutions and tried to tied the score once again, but than Rabotnicki put Filip Petkovski in the game and he scored for 1:3 just four minute after he came in. The win was secured by newcomer Vlatko Grozdanoski in the 88 minute for a final score of 1:4. The return leg will be played in Skopje on 7 July.

Lilleküla Arena in Tallinn, Estonia
Referee: Alan Mario Sant (Malta)
Scorers: Epikhin 34′ – Velkoski 16′, Manevski 51′, Petkovski 73′, Grozdanoski 88′
Red cards: /
Yellow cards: Leontovitš, Epikhin, Fyodorov, Grozdanoski.
Trans: Vyalchinov; Rimas, Grigorjev, Kitto (c); Epikhin, Bazyukin (59′ Strockis), Kazakov (61′ Plotnikov), Bezykornovas; Abramenko, Leontovitš (55′ Fyodorov), Čekulajevs. Manager: Aleksei Yagudin.
Rabotnicki: Dimitrievski; Lazarevski, Kumbev, Stojanov (69′ Petkovski), Bogdanovik; Petrovik (82′ Micevski), Todorovski, Grozdanoski, Manevski (90′ Angelov); Vujčić, Velkoski. Manager: Goran Petreski.