The Stuttgart director of sport represented both clubs during his playing career and, although he would favour the points for his current club, he would not begrudge his former club another Bundesliga victory.
"I have good memories of Berlin," he said. "I won the DFB-Pokal with them."
Stuttgart's own memories of games against Hertha are not so positive, on the other hand. They have lost 20 and drawn 15 of their previous 56 meetings with the Old Lady just holding the upper hand.
"That's partly my fault," joked Bobic, who was frequently on the winning side in these duels as a Berlin player.
"But these statistics really do look bad and I hope we can level things up tomorrow night."
To bring the stats back on an even keel, Stuttgart need to build on their 6-2 win over Hoffenheim a fortnight ago, a result which ended a three-game losing streak at the start of the season.
That should be a starting point for the Swabians, however, and not a result they can now relax after.
"There is no reason to be euphoric," said coach Thomas Schneider on his club's website. "There were things in that game too which we have to work on if we want to continue being successful."
Avoiding a similar fate to Hoffenheim is the main concern of Hertha coach Jos Luhukay, who has warned how easy it is to concede when Stuttgart are on top of their game.
"We want to beat Stuttgart but it will be very difficult," he said at a press conference.
"They are strong and they are good on the counter-attack with fast players up front and we've got to try to prevent that.
"It's not going to be easy to succeed over 90 minutes, but of course we want to get back to winning ways again.
"It's going to be intensive, but it's motivating and attractive."
He is set to show his faith in forward Ronny as a replacement for the injured Alexander Baumjohann, who tore cruciate knee ligaments a fortnight ago.
Schneider is not expected to make any changes to the side which earned Stuttgart's first points of the season.