Several highlights of Rooney's playing career with DC had come against Orlando.
The former England captain had five goal involvements in three meetings with Orlando, netting in both matches in 2019 – including a stunning strike from his own half.
But the most iconic moment of Rooney's MLS stint came in his first clash with the Lions in 2018.
The forward provided two assists, including a remarkable intervention to snatch a 3-2 win in the 96th minute, with Rooney tracking down a counter-attack – as Orlando's Will Johnson raced towards an open goal – and then crossing for Luciano Acosta's decisive header.
His coaching bow was similarly sensational, as DC still trailed to Junior Urso's early strike entering second-half stoppage time.
But a pair of late goals from Chris Durkin, in the 91st minute, and Taxi Fountas, in the 95th, ensured a winning start for Rooney, who had been confident the chances would come.
"I told them they'd win the game," Rooney said of his half-time message to the MLS strugglers. "I believed we'd win the game.
"But the one thing we had to do was up the tempo. We were moving the ball across the back and with the goalkeeper side to side, and it was too slow. We were allowing Orlando to shift across and not really making them run as hard as we wanted them to.
"That was the big difference second half, the tempo with which we moved the ball and really made Orlando suffer and work and run.
"When a team's doing that, then gaps appear. We have to take advantage of those gaps, and we did."
It was just the 10th instance in MLS history of a team trailing at the start of stoppage time and still winning, with DC accounting for three of those.
Rooney acknowledged the nature of the victory could be vital for confidence moving forward.
"'Character' is a big word I've used over the last couple of weeks with the team," he said. "We need to be a team which shows a lot of character and fight and togetherness."
Rooney added: "I think [it is important] for the players, more than myself. I think the players needed that.
"This season has to start now. They've had some bad results in the first half of the season, and I think tonight the fashion we won the game – coming from a goal behind, scoring two late goals, the subs who came on were excellent...
"But we've got another tough game on Wednesday. We can't rest and think we've won a game; we have to be consistent, we have to go on a run."