They kind of had it in the Super anime during the sparring episode with Gohan. Also, technically the Piccolo we know since his merging with Kami isn't Piccolo anymore beyond a name for simplicity as he says himself and shows through his change in demeanour, so there wouldn't be the personal stake or drive as strong as that for Goku's other rivals during their rematches and would be more fanservice if anything rather than being in service to his character.
At this point, it would be almost impossible to pull it off when Goku keeps leaving Piccolo in the dust. Then again, Piccolo has seemingly improved to the extent he seems on par with Gohan currently, so it may be possible if Toriyama cuts him a break and gives him some new power up, maybe a Namekian god form as a callback to part of him having once been Earth's Kami.
