A long-standing knee injury caused the 35-year-old United States international to bring his playing career to an end this week and, rather than being in the Niedersachsenstadion dressing room on Saturday, he will be supporting his former team-mates from the stands.
"I didn't have to bow out on a Bundesliga game - I've played plenty of them," said Cherundolo, who made only two appearances this season, totalling 302 in his career.
"Now I'm looking forward to telling the lads what to do rather than having to do it myself."
Cherundolo will begin his new role as assistant coach for the reserve team in the coming weeks after ending a 15-year playing career which saw him represent only one club - Hannover.
"I think there were many great moments," Cherundolo said. "For me, the most beautiful thing is to win as a team and we at Hannover did so well because we were always a strong team.
"This was our strength and this will continue to be the way at Hannover. It's my job now to pass that on to the younger ones."
Cherundolo can expect an emotional send-off from the Hannover fans prior to Saturday's match.
"It's quite extraordinary that one player spends so long with just one club, and thoroughly identifies with them," said club president Martin Kind.
"We've been in the Bundesliga unbroken for 12 years, and Stevie's been involved all the way.
"He was highly accepted in the team and was an extraordinary role model."
While Cherundolo was announcing his retirement, Dortmund were busy booking their place in the last eight of the Champions League.
A 2-1 defeat to Zenit St Petersburg on Wednesday night may have been a disappointing result, but thanks to a 4-2 win in the away leg, the Westphalians went through on aggregate.
"All that matter in the end is that we've gone through," said defender Mats Hummels.
"Given our injury situation, we've got to say we'll be the outsiders whoever we play in the quarter-finals."
They will be favourites on Saturday, though, even if they have also lost Marcel Schmelzer to injury.
The Germany full-back has been ruled out for four weeks due to a groin injury he picked up in midweek.