Both aiming to become one of six sides to reach the Champions League group stages through qualifying, Rakow Czestochowa and Flora kick off their first-round tie on Tuesday.
The Polish champions will welcome their Estonian counterparts to Rakow's Miejski Stadion Pilkarski, ahead of the return in Tallinn next week.
Match preview
The 2023-24 Champions League's preliminary rounds commenced at the end of last month - just weeks after Manchester City were crowned European champions - with a mini-tournament in Iceland.
Now, a number of national champions join the fray, including last term's Ekstraklasa winners Rakow Czestochowa, who had finished runners-up in both previous seasons.
Only promoted to the Polish top flight in 2019, the Czestochowa-based club from the district of Rakow finished nine points clear of established giants Legia Warsaw to claim the title, having twice won the Polish Cup and Super Cup in the past three years. They will defend the latter on Saturday, against Legia.
The Medaliki conceded a league-low 24 goals on route to glory last season, while scoring an Ekstraklasa-high 63 at the other end, so can certainly pose a threat to some of the bigger names in the scrap for a Champions League place.
With plenty of recent experience in Europa Conference League qualifying, where they have won seven of 12 matches - albeit without reaching the group stage - Rakow now aim to avoid another return to that competition, which will be the consequence for losing in the first qualifying round.
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Starting life under new coach David Szwarga, after title-winning boss Marek Papszun departed, Rakow recently held a training camp to prepare for the upcoming campaign, with a 2-1 victory over Romania's Universitatea Cluj capping off their stay in Austria, thanks to first-half goals from Deian Sorescu and Fabian Piasecki.
Flora, meanwhile, have had no need for such a warm-up, as they are in the middle of defending their domestic title, currently topping the Meistriliiga ahead of local rivals Levadia Tallinn.
After finishing the 2021 season as runners-up, Flora won a 14th Estonian championship title in 2022, earning 97 points and matching Levadia's 2009 record of most points accrued in a single campaign.
They also boast recent European experience, having become the first club from Estonia to reach a UEFA competition group stage when successfully qualifying for the 2021-22 Europa Conference League. On matchday five, Flora made more history by beating Partizan Belgrade 1-0 in Tallinn, via a Martin Miller goal, thus becoming the first Estonian side to win a UEFA group game.
Coach Jurgen Henn - who has been in charge for five years - has since gone on to build a team seeking back-to-back Meistriliiga crowns, and they have conceded just nine times in 19 league matches so far this year, including Friday's goalless draw at mid-table Paide.
Team News
Joining a multinational squad in Czestochowa, Greek goalkeeper Antonis Tsiftsis recently arrived at Rakow from Asteras Tripolis on a season-long loan with an option to buy.
The 23-year-old now competes with fellow new-boy Kacper Bieszczad and former Bosnia Under-21 international Vladan Kovacevic to start for the hosts, who have also signed German forward John Yeboah, scorer of 10 goals in the Polish top flight last term for Slask Wroclaw.
However, during the training camp in Austria, another recent recruit, Bosnian defender Adnan Kovacevic, sustained a thigh injury and will be out for six weeks.
That came as a further blow to David Szwarga's plans, after Spanish midfielder Ivan Lopez - who scored nine league goals last season - suffered an ACL injury just days earlier; he must now undergo reconstruction surgery and begin the long process of rehabilitation.
Meanwhile, Flora will benefit from a more settled side, as they have been engaged in domestic action for several months now; therefore, the visitors' lineup should be similar to that which featured against Paide last week.
Estonia internationals Martin Miller and captain Konstantin Vassiljev will play key roles in midfield, while Rauno Alliku leads the line up front. The latter has racked up more than a century of goals for the club across a lengthy career.
Rakow Czestochowa possible starting lineup:
Kovacevic; Petrasek, Arsenic, Svarnas; Tudor, Papanikolaou, Lederman, Carlos; Yeboah, Piasecki, Gutkovskis
Flora possible starting lineup:
Grunvald; Lilander, Kuusk, Hussar, Seppik; Kreida, Vassiljev, Miller; Ojamaa, Alliku, Reinkort
We say: Rakow Czestochowa 2-1 Flora
Rakow have risen through the ranks in Polish football and their next step is making an impact on the continental stage. While they should have too much firepower for Flora on Tuesday, a lack of match-fitness could prove a limiting factor, so it may be only a slim advantage they take to Tallinn next week.
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