What he's yet to experience in his career is the NCAA tournament.
But unlike years past, when Ole Miss would come close only to fall short of the ultimate goal, Holloway said the Rebels now have what he believes was the missing ingredient heading into the 2012-13 season. Something they haven't had before.
A marquee shooter in the form of junior college transfer Marshall Henderson.
"I think Marshall gets us there," Holloway said. "Have we ever had a straight shooter than can shoot like that? I don't think we've ever had one. I think it gets us there. We've got a lot of depth, a bunch of good guys. I think that gets us there."
Ole Miss' NCAA tournament drought is well-documented. The Rebels haven't made the field since 2002. Head coach Andy Kennedy led five of his six teams to 20-win seasons, but all five of those seasons ended in the NIT.
On Kennedy's side in year seven is a veteran team led by seniors Holloway, Nick Williams and Reginald Buckner. Add in returning point guard Jarvis Summers, and the Rebels return four starters that combined to start 117 games last season and boast 228 career starts.
However, Henderson could very well be the key. He led Ole Miss with 19 points in a 77-62 exhibition win over Montevallo on Monday.
"We feel the NCAA tournament, obviously, is the goal," Henderson said. "We feel that once we get to the NCAA tournament, we can make some noise."
Ole Miss was sloppy against Montevallo, finishing with 15 turnovers. The Rebels shot 52 percent from the game, but allowed 19 offensive rebounds. There was some good and some bad.
The game, Kennedy said, was a good teaching tool.
"Montevallo's not a bad team," he said. "They played Purdue pretty close. I knew they were going to be well-prepared and pretty tough. I thought they were more physical than us at times, especially when we had our young guys out there.
"I got done what I needed to get done. I'll be able to use (the game) to try to show guys the areas in which we're week as we approach the real season."
Ole Miss officially opens its season tonight against Mississippi Valley State. The Delta Devils made their fifth NCAA tournament appearance last season, falling in the opening round to Western Kentucky.
First-year head coach Chico Potts takes over for Sean Woods, who left for Morehead State, and must replace 98.9 percent of his team's scoring from a year ago.
"Last year, they go to the NCAA tournament," Kennedy said. "They lost most of their players. I really don't know what to expect. We go into it a little bit blind, which is not bad. It makes me a little bit uncomfortable, obviously, but I think it's good for our guys to figure some things out."
Cox on the mend; Carter still suspended:
Junior forward Demarco Cox had off-season surgery for a stress fracture in his foot. His rehabilitation is going well, Kennedy said, and he's set to resume on-floor activity next week.
Cox was seven weeks post-operation Tuesday. Kennedy said following the exhibition win the goal is for Cox to return to basketball action at eight weeks.
"Then it's just a matter of getting back in rhythm and getting back in shape," Kennedy said.
Forward Jason Carter remains suspended for a violation of team rules. Kennedy announced the suspension Monday night. Guard Derrick Milliinghaus, who didn't play against Montevallo due to an academic issue, is expected to play against Mississippi Valley State.
With Cox and Carter out, freshman forward Terry Brutus saw added minutes vs. Montevallo.
"I thought he was good at times," Kennedy said. "First time he's been against somebody else in this building, so he was out of place at times."
"He can be big, man," Holloway said of Brutus. "He can get minutes, improve, while they're out. That's big for him."