When Indiana Jones broke into Castle Brunwald to rescue his father, this Prinicpal SS officer and two guards burst into the room and demanded the Grail diary. Following an argument between father and son, Jones knocked the officer backwards and shot him along with the two guards behind him.
Behind the scenes
The SS officer was played by Luke Hanson.
Although seeming to simply be knocked unconscious after being knocked down in the film (as when Indy and Henry run from the room the officer is visibly breathing), the novelization of Indiana Jones and the Last Crusade specifically has him being shot along with the guards.