Still winless this season, the Serie A side meet experienced Shakhtar in their first league-phase fixture, with the Ukrainian champions keen to improve their sub-par record in Italy.
Match preview
Now embarking on just their second season in UEFA's top club competition, Bologna last featured at this level during their mid-60s heyday, when losing via a coin-toss to Anderlecht in the 1964 preliminary round.
Much has changed since then, and the Emilian side will this week become one of five clubs to make their Champions League debut in the competition's newly expanded format for 2024-25.
Bologna will be the 11th Italian team to appear in the tournament proper, after the seven-time Scudetto winners set a new club record of 68 points last season, recording their highest league finish since 1967.
Having inspired an unheralded side to fifth place in the final standings, Thiago Motta accepted an offer from Juventus, so former Fiorentina boss Vincenzo Italiano - beaten in both of the last two Europa Conference League finals - was brought in.
However, Italiano is still awaiting his first competitive win, having overseen disappointing home draws either side of a 3-0 defeat to Napoli; then, last weekend, Bologna had to come from two goals down to rescue a point against promoted Como.
A squad stripped of star men Joshua Zirkzee and Riccardo Calafiori - both departed for England in the summer - needed goals from substitutes Santiago Castro and Samuel Iling-Junior to save the day, and they occupy 17th place in the early Serie A standings.
The Rossoblu will now take their first step into any European competition since losing an Intertoto Cup clash against Fulham in 2002, and they will defend a proud record at Stadio Dall'Ara, where they have never lost in Europe, winning 15 of 23 matches to date.
While Bologna are Champions League rookies, Shakhtar Donetsk reached the quarter-finals as recently as 2011 and have featured in all but one of the last 15 years.
Shakhtar only missed out on the knockout rounds last term due to a crucial defeat at Porto on the final matchday, but they have now been eliminated in the group stage for six seasons on the spin.
After dropping down into the Europa League, the Miners were beaten by Marseille in the knockout-round playoffs, though that did not taint an otherwise superb 2023-24 campaign.
Under Croatian head coach Marino Pusic, Shakhtar claimed a 15th Ukrainian Premier League title by finishing two points clear of old foes Dynamo Kyiv, before going on to lift the cup and complete their ninth domestic double.
This term, though, they have lost twice already, having suffered only three defeats throughout all of last season. An Artem Bondarenko hat-trick helped them to a 5-2 home win over Karpaty Lviv at the weekend, but they only sit sixth after five matches.
Already estranged from their home city by war, Shakhtar must now try to pick up points on the road: they have won just twice in their last 11 Champions League away matches before heading to Italy, where they have lost 10 of 15 previous meetings with Serie A sides.
Bologna form (all competitions):
Shakhtar Donetsk form (all competitions):
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Team News
Bologna's injury woes have started to clear, just ahead of their European comeback, as defensive duo Emil Holm and Martin Erlic joined Swiss winger Dan Ndoye on the bench in Como.
Oussama El Azzouzi and Nicolo Cambiaghi, however, suffered serious knee injuries last month and are out for the long term; Scottish star Lewis Ferguson is still working his way back to fitness from an ACL injury.
The hosts' captain, Riccardo Orsolini, scored from the spot on Serie A's opening matchday and has therefore found the net in seven different seasons for the club. The Italy international should start in support of either Santiago Castro or Thijs Dallinga up front.
Meanwhile, Shakhtar Donetsk striker Danylo Sikan registered a tally of four goals from six games in last season's Champions League and is now his club's joint-top scorer this term on three goals.
Recently on the scoresheet for Ukraine in the UEFA Nations League, Georgiy Sudakov created the most chances (10) and completed the most passes (229) of any Shakhtar player during last year's group stage.
He may now be joined in midfield by one of the visitors' customary Brazilian contingent: Marlon Gomes returned from a hamstring injury at the weekend, following a month-long layoff.
Bologna possible starting lineup:
Skorupski; Posch, Beukema, Lucumi, Miranda; Freuler; Orsolini, Aebischer, Moro, Ndoye; Castro
Shakhtar Donetsk possible starting lineup:
Riznyk; Konoplya, Franjic, Bondar, Pedrinho; Bondarenko, Kyrskiv, Sudakov; Zubkov, Sikan, Kevin
We say: Bologna 2-2 Shakhtar Donetsk
While Shakhtar's experience should count in their favour, the Ukrainian champions do not tend to travel well and could come unstuck in Emilia-Romagna.