Stuttgart, meanwhile, have not lifted the DFB-Pokal for over 25 years, when Giovane Elber's brace sunk third tier outfit Energie Cottbus in the 1996-97 final.
Match preview
More recently, Stuttgart have been battling to avoid being relegated to the second tier, with their 2-1 victory at home against Borussia Monchengladbach on Saturday finally lifting them outside of the relegation places.
Sebastian Hoeness has made a hugely positive impact since replacing Bruno Labbadia in early April, collecting eight points from four unbeaten matches in the Bundesliga, as well as guiding them into the last four of the DFB-Pokal with a tight 1-0 win away to Nuremberg in the 40-year-old's first game in charge.
Should the former Hoffenheim boss be able to take Die Schwaben into their first major final since losing 3-2 to Bayern Munich a decade ago, on top of helping them secure their top-flight status for another campaign, the signs would be bright that Stuttgart can begin to build towards reaching a level befitting of their gigantic status in German football.
The next few days are set to prove pivotal in terms of determining whether Hoeness proves successful on both domestic fronts, with a trip to the capital to take on relegation rivals Hertha Berlin awaiting them on Saturday after hosting Frankfurt on Wednesday evening.
Frankfurt, meanwhile, have far less riding on their final four league games of the season, having failed to win any of their last nine Bundesliga matches to drop to ninth in the table.
Die Adler played out a fourth consecutive 1-1 draw at Deutsch Bank Park in the Bundesliga against Augsburg at the weekend, with Oliver Glasner's side only generating one shot on target across the 90 minutes. As such, they could have no complaints when Ermedin Demirovic equalised for the visitors two minutes before the hour mark to take home a crucial point for his struggling side.
Any Stuttgart fans believing that their forthcoming opponents' dramatic loss of form in recent weeks suggests they are in store for an easy match on Wednesday should remind themselves that almost the exact same process happened with Frankfurt last season, when they clearly prioritised chasing success in the Europa League ahead of their league results.
Indeed, Glasner's side are almost certainly assured of claiming a top half finish in any case, so the 48-year-old will be desperate to win his second major trophy in only two seasons at the club following his move from Wolfsburg in the summer of 2021.
Stuttgart DFB-Pokal form:
W
W
W
W
Stuttgart form (all competitions):
L
W
W
D
D
W
Eintracht Frankfurt DFB-Pokal form:
W
W
W
W
Eintracht Frankfurt form (all competitions):
D
W
L
D
L
D
Team News
Stuttgart will hope to have their star striker Serhou Guirassy available to start, with the 27-year-old substituted early in the second half against Gladbach on Saturday. The likes of Tiago Tomas, Tanguy Coulibaly and Chris Fuhrich will all be on standby to replace Guirassy should he be ruled out of selection on medical grounds.
Otherwise, Hoeness appears to have a fully fit squad to select from, so it remains to be seen whether he will rotate ahead of a hugely important league clash against Hertha less than 72 hours later.
For that reason, it would be little to surprise to see the likes of Florian Muller, Fuhrich and Genki Haraguchi come into the hosts' starting XI, but with tangible success in the form of a trophy only two victories away, Hoeness is unlikely to make too many changes.
Frankfurt, meanwhile, are expected travel without Kristijan Jakic, Evan Ndicka, Philipp Max and Hrvoje Smolcic due to injury, but they will be desperate to have Randal Kolo Muani available once again after the France forward missed the weekend's draw against Augsburg with an adductor issue.
In all likelihood, Glasner was probably resting Kolo Muani as a precautionary measure ahead of a more important fixture, but Rafael Santos Borre will be called upon to lead the visitors' attack should the 24-year-old fail to prove his fitness in time.
Jesper Lindstrom could start after making his own comeback from an ankle injury to appear from the bench against Augsburg, while Djibril Sow should also return to the engine room after being rested on Saturday.
Stuttgart possible starting lineup:
Muller; Vagnoman, Mavropanos, Zagadou, Anton, Sosa; Haraguchi, Karazor, Endo; Silas, Guirassy
Eintracht Frankfurt possible starting lineup:
Trapp; Tuta, Hasebe, Lenz; Ebimbe, Rode, Sow, Knauff; Lindstrom, Gotze; Kolo Muani
We say: Stuttgart 2-1 Eintracht Frankfurt
Much will hinge on whether Guirassy and Kolo Muani - who are comfortably these two sides' most dangerous attackers - are able to start in this huge semi-final clash, but Frankfurt are clearly lacking momentum after enduring a winless run of nine league matches in recent times.
Glasner's side are suffering with several injuries to key defenders, too, and we can envisage Stuttgart using their strong form under Hoeness and a boisterous Mercedes-Benz Arena in their favour to reach their first final in 10 years.