This game marked a new lease on his football life.
It had been a tumultuous week for Masoli, one where he was initially ruled ineligible for the season by the NCAA.
But on Friday, a subcommittee overturned the ruling, allowing the former Oregon quarterback to dust off his newly-assigned No. 8 jersey and participate in the team's season opener.
"It was great, just taking the field for the first time with my teammates," he said. "I was nothing more than happy. I was just glad to be out there. (The week's) been a little rocky. I just hung in there and kept encouraging the guys."
But the end result was nothing like he would have hoped.
Jacksonville State stunned Ole Miss, 49-48, in double overtime. The Rebels were outscored 24-3 in the second half to tie the score, before the Gamecocks sent Masoli and his team into the Ole Miss locker room in collective shock.
Ole Miss head coach Houston Nutt turned to Masoli in both overtime periods. Ole Miss scored in each series.
"That was a heart-breaker. Definitely," Masoli said. "It's just tough. "We have to learn from it. We can't let it happen again."
Masoli has been here before. While quarterbacking Oregon, he saw Boise State pull an upset in Boise. Still, the Broncos were ranked in the Top 25 nationally. JSU is an FCS opponent. Even worse, the Gamecocks trailed, 31-10, at halftime.
"Last season when we lost to Boise, it was a big blow for us," Masoli said. "We all thought we were going to win that. But one of the things I did learn from that is you get better. You get better every day, one day at a time. Last year, (Oregon) came on top in the conference.
"Those are still our goals. We can still do that and everybody understands that."
Sophomore Nathan Stanley got the start and deservedly so. Stanley toiled two seasons behind Jevan Snead for his shot as a Southeastern Conference quarterback, not to mention his experience in Ole Miss' offensive playbook.
Masoli, meanwhile, waited patiently on the sidelines. He knew he would play. It was only a matter of when. He saw Stanley throw two touchdowns in his first three passing attempts, both in the first quarter. Stanley was doing exactly as he was expected to do – lead the offense without a glitch.
Then it happened.
Later in the quarter, and with Ole Miss holding a 14-3 lead, Stanley dropped back to pass and looked downfield. He felt the rush, Jacksonville State's Jamison Wadley rushing furiously up the middle.
Stanley attempted to make a miracle play, but ultimately surrendered a touchdown to Jacksonville State via fumble recovery. And as Wadley was celebrating in the end zone, Masoli began taking snaps close to the Ole Miss bench.
"The (linebacker) came off the edge untouched," Stanley said. "I've got to do a better job of securing the ball. I've got to bring into my body, instead of doing what I did."
Masoli jogged out to lead his offense on its fourth position. After a six-yard rush by Enrique Davis, he found tight end Ferbia Allen for 10 yards, his first career completion. He followed with a rush of 15 yards on an option-read, before the drive stalled five plays later at the JSU 1-yard line.
"As the game went on today, we were feeling pretty confident," Masoli said. "Then in the second half, we got a little sluggish. You've just got to tip your hat to Jacksonville State. They took advantage of it."
Masoli showed flashes, if in a small variety, of his former Heisman candidacy. He improvised and aimed for the spectacular, even connecting with Davis on a jump pass which turned into a 16-yard gain.
But he had his troubles, too. He missed an open receiver down the middle with Ole Miss threatening inside opposing territory, resulting in an interception by Gamecock defensive back Keginald Harris. Jacksonville State promptly scored on its next possession.
"I did alright," he said. "The interception was on me. I shouldn't have done that."
All in all, he accounted for 138 total yards, finishing 7-of-10 for 109 yards and one interception. Stanley was 6-of-10 for 133 yards, 2 touchdowns and one fumble.
How Ole Miss utilizes its quarterbacks moving forward is an interesting debate. Stanley and Masoli are likely to comprise Nutt's two-quarterback system, with junior Randall Mackey used sparingly, if at all.
"It's definitely a tough loss," Stanley said. "You want to win your home opener. It's a tough pill to swallow. We can't dwell on it. We have to put it behind us and get ready for next week."