Both sides are looking to build on successful seasons, after the hosts gained promotion to Germany's second tier, and Frankfurt won the Europa League to directly qualify for the Champions League group stage.
Match preview
Magdeburg, who compete in a 30,000-seated stadium at MDCC-Arena, have never progressed beyond the quarter-finals of the DFB-Pokal. That achievement came in the 2000-01 campaign, when they lost 1-0 to eventual champions Schalke 04.
However, they are the only former East German side to lift a European trophy after winning the UEFA Cup Winners' Cup in 1974, having won the former East German top flight on three occasions in the 1970's prior to the nation's reunification.
Der Club fell on hard times thereafter, only returning to the third tier of German football - and therefore reassuming professional status - in 2015. They have flirted between 2. Bundesliga and 3. Liga since, with manager Christian Titz guiding his side to promotion last season after amassing 78 points from 36 games to end as champions.
One win and one defeat from their opening two games back in the second tier suggests surviving another instant relegation should be possible for them. In the meantime, though, they will focus on causing an upset in front of their passionate home support on Monday.
Frankfurt, who have won the DFB-Pokal on five occasions - most recently in 2018 after impressively beating Bayern Munich 3-1 in the final - could be forgiven for thinking they have bigger fish to fry than Germany's domestic cup this season.
After guiding Wolfsburg to a fourth-placed finish and Champions League status in the 2020-21 season, Oliver Glasner worked his magic once again by taking Die Adler all of the way in the Europa League in his debut campaign at the club.
The German side were pushed all of the way by Rangers in the final in Seville, ultimately winning on penalties after a 1-1 draw. The victory crowned Franfurt's first European honour for 32 years, and ensures they will dine at Europe's top table for only the second ever time after reaching the European Cup final all the way back in 1960.
An unbeaten pre-season period suggests Glasner's side remain full of confidence ahead of the coming campaign, with Monday's trip to Magdeburg an interesting test ahead of kicking-off the 2022-23 Bundesliga season against champions Bayern on Friday night.
Magdeburg 2. Bundesliga form:
Eintracht Frankfurt pre-season form:
Team News
Magdeburg look set to be without Maximilian Frankze and Luca Schuler due to serious muscle tears.
Left-winger Florian Kath will also be absent as he continues with his battle against mononucleosis.
Titz is likely to choose the same XI which impressively defeated Karlsruher SC 3-2 away from home last weekend, with Andreas Muller, Baris Atik and Moritz-Broni Kwarteng hoping to get on the scoresheet once again.
Frankfurt have a couple of injuries in defence to contend with, as Jerome Onguene and Aurelio Buta will not make the trip due to muscle and knee issues respectively.
Having only come on at half-time as one of many substitutes, Onguene was replaced by Marcel Wenig during the second-half of his side's 5-0 rout of Astoria Walldorf last weekend.
Glasner may choose the same starting XI from that victory, with new signing Mario Gotze set to make his competitive debut for the club.
Filip Kostic should be involved from the start again despite rumours linking him with a move to Premier League side West Ham United, who have had a bid rejected for the Serbian wing-back.
Magdeburg possible starting lineup:
Reimann; El Hankouri, Sechelmann, Bittroff, Bell Bell; Muller, Conde, Krempicki; Ceka, Kwarteng, Atik
Eintracht Frankfurt possible starting lineup:
Ramaj; Toure, Tuta, Smolcic; Knauff, Kamada, Sow, Kostic; Lindstrom, Borre, Gotze
We say: Magdeburg 1-3 Eintracht Frankfurt
We expect to see an open, entertaining cup tie at the MDCC-Arena on Monday.
Madgeburg should benefit from having played two competitive matches compared to Frankfurt whose season starts here, but the Europa League winners should have too much quality if they can ride out the hosts' early storm.