The two second tier sides are meeting in the Cup for the first time since their fateful first-round tie 15 years ago, a game which unleashed the biggest betting scandal in German football history.
In August 2004, rank outsiders Paderborn came from 2-0 down to claim a sensational 4-2 victory over then Bundesliga side Hamburg, assisted along the way by a string of questionable decisions from referee Robert Hoyzer.
Hoyzer sent off Hamburg's Emile Mpenza with the score at 2-0 and awarded two highly controversial penalties to help Paderborn fight back to win 4-2.
The referee later admitted to deliberately manipulating games in both the German Cup and Bundesliga 2 for financial gain.
He was sentenced to two years and five months in prison for aiding and abetting organised fraud, and was given a lifelong ban from football by the German FA (DFB).
Klaus Toppmoeller, who was head coach of Hamburg at the time of the scandal, said that Hoyzer's deception had a lasting effect on his life and career.
"It was like the end of the world for me," Toppmoeller told AFP subsidiary SID this week.
"I am somebody who grew up playing football and wanting to win fairly. That someone would come and cheat like that was unfathomable to me."
"Some of our players heard him tell the Paderborn players to just keep playing the way they were, and he would 'take care of the rest'," he said.
Toppmoeller said that he left Germany as a result of the scandal, turning down offers from Cologne and Hoffenheim to take over the Georgian national team.
Paderborn and Hamburg are now more evenly matched than they were back in 2004, with both teams vying for promotion to the Bundesliga this season.
Hamburg are clinging on to an automatic promotion spot in second place in Bundesliga 2, while Paderborn are six points behind them in fourth.