Sitting astride the highway to Rome, the historic abbey of Monte Cassino — founded in 524 AD by St. Benedict himself — dominated the surrounding landscape from its strategic hilltop. German paratroopers did not initially occupy the venerable site, but after American bombers destroyed the buildings they turned the rubble into a nearly impregnable fortress. Between January and May 1944, American, Polish, Indian, New Zealand and British troops launched four major attacks on the position, and many minor ones. Three times the Germans drove them back, until finally on 18 May 1944 a troop of Polish Lancers raised their red-and-white pennant over the ruins. Over 50,000 Allied soldiers and more than 20,000 Germans fell in the struggle for Monte Cassino.

The battles took place in the flat, muddy plains of Liri Valley and the steep mountain slopes of Monte Cassino, often in unpredictable winter weather. The Rapido River running around the base of Monte Cassino was only about 16 meters wide, but was up to 4 meters deep and flowed very fast, presenting a major obstacle. Cassino '44 is a complete boxed game in the Panzer Grenadier series by David Murray, covering all four of the battles. From the initial American assaults through the final Polish conquest, every stage of the battle is depicted in scenario form with two lengthy campaign games covering the entire affair.