In two of his previous three seasons at Ole Miss, his teams have flirted with reaching the NCAA tournament - be it a 20-win season a year ago, or in 2009, when the Rebels finished the year with 24 wins after a run in the NIT.
Seasons, at least for contending teams, are defined by the last few weeks of February and early days of March. Well, the calendar has turned. And for an Ole Miss team quite familiar with the bubble, the time is now.
"I think we've done that almost every year," Holloway said. "We've had to win to get in every year."
These final three games of the regular season serve as Holloway's last chance to break through. He, like his head coach, has never reached college basketball's biggest stage.
"I do feel a sense of urgency," said Andy Kennedy, who despite being the winningest coach in Ole Miss history, is still searching for that ever-elusive NCAA tournament bid in his seventh season.
"If you don't have it now - and there's only about 10 days left in the regular season - then I'm not sure you're ever going to find it. We understand the importance of each and every one of these games."
The Rebels are 21-7 overall and 10-5 in the Southeastern Conference. But while their win total is nice, their resume is lacking. Ole Miss is short on quality wins - the quantity over quality argument.
Let's do the math. Ole Miss enters Saturday with an RPI ranked No. 55 in the country by RealTimeRPI. However, the Rebels are just 1-4 against the RPI top-50. Against the top-100, they're 5-6.
Mississippi State checks in at No. 239 in the RPI, while Alabama (62) and LSU (92), the Rebels' remaining opponents, are both top-100 teams.
"We're just taking it a game at a time and staying focused," sophomore guard Jarvis Summers said. "We've got three games left. We're trying to stay poised and come together as a team and do what we have to do."
What Ole Miss has to do is win.
In his recent bracketology, ESPN's Joe Lunardi has Ole Miss as one of his "last four in." Jerry Palm of CBSSports.com, meanwhile, has Ole Miss as his "first team out."
What's in a number? Since the last major change in the RPI formula, which was first used for the 2005 NCAA tournament, no team with at least 24 wins from one of the big six conferences - ACC, Big 10, Big 12, Big East, Pac 10 and the SEC - has been left out of the Big Dance.
Coastal Carolina holds the dubious distinction of being the team with the best record (24-5) to be left out of the tournament. Again, though, it wasn't/isn't a big six team. Virginia Tech was 23-8 in 2010 and fell short.
So while Ole Miss' resume may lack substance, the Rebels have history on their side should they keep stacking wins together.
Tip-off between Ole Miss and Mississippi State (7-20, 2-13 SEC) is set for 4 p.m. The Bulldogs have lost 13 games in a row.
"We can't overlook anybody," Holloway, Ole Miss' all-time leader in rebounds, said. "I expect them to still play hard."
Mississippi State is in the midst of its worst season since 1986-87, when the Bulldogs posted a 7-21 record. Ole Miss took a 93-75 win earlier this season. The Rebels are looking for their first season sweep of Mississippi State since 1998.
The Bulldogs hold a 91-24 advantage in Starkville, where Ole Miss last won in 2009.
"We're still going to have to guard," Summers said. "They're playing Ole Miss. It's a rivalry. They're going to give 110 percent."
"There's no question it's going to be a very competitive game," Kennedy said. "It always is. I don't know what their mental state is, but I know that they'll be excited about hosting us. Honestly, I know that they'll be focused and excited about the opportunity."