Both aiming to end a long wait for Coppa Italia glory, AC Milan and Bologna will clash on Wednesday night, when this year's final takes place at Stadio Olimpico.
The clubs met as recently as last week in Serie A, as Milan fought back to win 3-1 on home turf, but they now reconvene in Rome with silverware at stake.
Match preview
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In a curious precursor to the cup final, Milan met Bologna at San Siro for Serie A's Friday night contest, and a comeback win helped the hosts draw within two points of their visitors in the standings.
After falling behind to Riccardo Orsolini's latest strike of a superb individual season, the Rossoneri were set for a home defeat, but the second-half introduction of Santiago Gimenez turned the game on its head - the Mexican striker scored twice, either side of Christian Pulisic's 11th league goal of the season.
As a result, Milan have finally won four straight games across all competitions for the first time this season - in fact, for a whole year - and they seem intent on finishing their chaotic campaign with a flourish. Benefiting from a new tactical system that has brought five wins from six matches, the Lombardy giants are starting to stir from their slumber.
Despite starting Sergio Conceicao's reign with victory in January's Supercoppa Italiana - when the tone was set for a series of fightbacks - they subsequently limped out of Europe and continued to toil in Serie A, where they are on course to finish outside the top six.
Yet, they recently defeated arch-rivals Inter Milan 4-1 over two legs to reach the Coppa Italia final, making it five games unbeaten against their Nerazzurri nemesis this season.
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Previously, they had reached the semis in style. Milan entered at the last-16 stage due to European commitments, following December's emphatic 6-1 demolition of bogey team Sassuolo by eliminating Roma, as Tammy Abraham bagged a brace against his parent club.
While rumours abound that Conceicao will not be retained for next term, he could still change that narrative by succeeding in another cup competition, having correctly pointed out that the Rossoneri last claimed two trophies in a season back in 2008.
After winning the Supercoppa against Inter, Milan now aim to remedy a relatively poor Coppa Italia record for a club of such stature: their sole triumph for almost half a century came 22 years ago.
Furthermore, success in Rome represents their most realistic route back into Europe. So, fans on the red-and-black side of Italy's second city will hope they can overcome a dismal domestic cup-final record that reads one win from the last six appearances.
More renowned for their relationship with the European Cup and Champions League, Milan have won the Coppa just five times to date - though history suggests an even greater burden will bear down on Bologna.
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While their opponents last lifted the Coppa Italia in 2003, Bologna have only done so twice before - most recently in 1974, when they beat Palermo on penalties.
This season's run took them past Monza and Atalanta BC to reach the semis for the first time since 1999, and Vincenzo Italiano's side then eased past ailing Empoli over the course of two legs, winning 5-1 on aggregate.
Swatting aside opposition who selected an unfamiliar team of youngsters and fringe players, instead choosing to focus on an ongoing relegation fight, Bologna cruised to a 3-0 victory at Stadio Castellani, as Orsolini's opener set the stage for a Thijs Dallinga brace.
They duly finished the job back on home turf, setting up a 15th meeting with Milan in the Coppa Italia: on the all-time ledger, the Rossoneri lead six wins to four so far.
After a run of 13 defeats and four draws against Milan in Serie A, Bologna finally broke that winless streak at Stadio Dall'Ara in February, but Friday's loss at San Siro dented their dreams of successive Champions League appearances.
Losing form just as the finish line appears, the Rossoblu have won none of three games since conquering Inter via Orsolini's late volley then beating Empoli four days later. Though they are still in the mix with two rounds remaining, the Emilian club now sit seventh in the table and must rely on others to make mistakes.
So, a defining fortnight awaits: after meeting Milan in Rome they must face old foes Fiorentina in the Derby dell'Appennino, before hosting Genoa on the final day of another eventful campaign.
Team News
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Milan will welcome back two key players that missed Friday's final warm-up at San Siro, as midfield regular Youssouf Fofana returns from injury and mercurial winger Rafael Leao has served a suspension.
A beneficiary of Sergio Conceicao's recent switch to three men at the back, Fikayo Tomori was forced off by a knock, but he should resume his role in central defence. Only Warren Bondo (ankle) and Riccardo Sottil (thigh) are set to miss out.
Once again, the Rossoneri's boss must choose between Santiago Gimenez, Tammy Abraham and Luka Jovic to start up front in a 3-4-2-1 formation, with either of the three to be supported by Rafael Leao and Christian Pulisic.
Meanwhile, Thijs Dallinga is set to beat Santiago Castro to selection as the spearhead of Bologna's attack, as the latter's breakthrough campaign has recently been hampered by a lingering foot problem.
The Dutch forward should be joined by Riccardo Orsolini, who will cut inside from his station out wide on the right - the Italy international has scored 15 goals across all competitions this season.
Swiss winger Dan Ndoye netted a late winner when Bologna met Milan at the Dall'Ara, but he must compete with Nicolo Cambiaghi and Benjamin Dominguez to feature on the left flank.
As Emil Holm is set to return from a layoff, he can compete with Lorenzo De Silvestri and former Milan captain Davide Calabria to start at right-back.
AC Milan possible starting lineup:
Maignan; Tomori, Gabbia, Pavlovic; Jimenez, Fofana, Reijnders, Hernandez; Pulisic, Leao; Jovic
Bologna possible starting lineup:
Skorupski; Calabria, Beukema, Lucumi, Miranda; Freuler, Ferguson; Orsolini, Odgaard, Dominguez; Dallinga
We say: AC Milan 2-1 Bologna (after extra time)
Italy's top comeback kings will lock horns again, as Milan have now earned 22 points from losing positions this season - including three when these teams met on Friday - while Bologna have battled back to gain 18.
So, there could be several twists and turns in the 'Eternal City', where it might take extra time to split two teams that sit side-by-side in Serie A.
The Rossoneri are in better form than their Rossoblu rivals, and with their trophy-winning know-how, they can lift the Coppa Italia for just a second time this century.
For data analysis of the most likely results, scorelines and more for this match please click here.
Jonathan O'Shea
