If you just mean the 5 best players, I would go with:
2000s: Gunn, Yates, Kanaskie, Pippen, Cuffee
2010s: King, Williams, Upshaw, Potts, Jones
If I need to put together an actual lineup of 5 guys to play a game, I would go with:
2000s: Kanaskie, Gunn, Calvin O'Neil (the senior year version of him), Yates, and Lee Nosse (everybody on the floor can score, Yates can flourish at the 4 spot, and O'Neil will keep perimeter defense strong even though Kanaskie's on-ball defense was not his strongest attribute).
2010s: Massey, Potts, Hammonds, King, and Jones (Massey and Hammonds will make life miserable for opposing guards; Jones will erase any effort to get to the rim; King and Potts are the 1-2 punch offensively and Hammonds will make people pay for leaving him open).
The 2010s would win. The toughest guys to leave off the squad for me are Marcos Knight and Laron Dendy. Knight is a better player than Hammonds IMO but I want a better combination of size on the court and I wouldn't have that with Potts and Knight playing together. Dendy was a good scorer and arguably a better facilitator as a big man, but King brings more offensive polish which I feel like this group needs since Massey and Jones are defense first guys.
Underrated guys from each decade: 2000s = Montarrio Haddock; 2010s = J.T. Sulton