One of the most successful clubs in Ukraine, Kyiv entered the competition with an established European pedigree, having previously participated in numerous Champions League/European Cup and UEFA Cup matches, as well as winning the 1975 and 1986 UEFA Cup Winners' Cups and the 1975 UEFA Super Cup. They had qualified for the 2008-09 Champions League, but their third-place finish in that competition's group stage sent them into the UEFA Cup Round of 32. There, they advanced over Valencia on away goals to set up the meeting with Metalist in the Round of 16.
Metalist, on the other hand, was a relative novice. The 2008-09 UEFA Cup was only their second time in European competition, with the first being the previous season's UEFA Cup (where they were eliminated in the first round by Everton). They got off to a much stronger start in 2009-10, opening their campaign with a 4-2 aggregate win over Besitkas to advance to the group stage. There, they finished at the top of their group, over more experienced European sides Galatasaray, Olympiacos, Hertha Berlin, and Benfica, then rolled over Sampdoria 3-0 in the Round of 32.
The Round of 16 match-up was held in Kiev, where the home side staked their claim with a 1-0 win thanks to a 54th-minute header from midfielder Ognjen Vukojevic (pictured). Metalist battled back to win the second leg 3-2, but Kyiv again advanced thanks to their two away goals.