While some have been highly successful, others quickly moved on after failing to make their mark on Wearside.
Three more Ross signings - Joel Lynch, Alim Ozturk and Jack Baldwin - departed the Stadium of Light yesterday, but what has become of the Scot’s recruits who had already moved on to pastures new?
We take a look at where they are now, and how they’ve progressed since leaving Sunderland:
1. Reece James
James was something of a surprise departure last summer as, shortly after triggering a one-year extension in his contract, he joined Doncaster Rovers. He remains with the South Yorkshire side having made 32 appearances this term. Photo: Naomi Baker
2. Dylan McGeouch
McGeouch failed to have a consistent run in the side under Ross, and it was no surprise when he was allowed to leave by new manager Phil Parkinson. He joined long-term admirers Aberdeen in January, and made nine appearances for the club before the season was halted. Photo: Getty Images
3. Glenn Loovens
Loovens has moved into scouting since his departure from the Stadium of Light and subsequent retirement - and has already stated his desire to help source players for former club Celtic. Photo: Naomi Baker
4. Jerome Sinclair
Sinclair could only muster two goals during an unsuccessful loan spell at Sunderland in the first half of the 2018/19 season. He spent the most recent campaign on loan at VVV Venlo, making 23 appearances and failing to score. They’ve already confirmed he won’t be back next season. Photo: Dan Istitene