After falling just short of the left-field fence in the eighth inning, the former first-round Draft pick completed the cycle with a two-run walk-off homer in the 11th to lead the Daytona Cubs past the Lakeland Flying Tigers, 6-4.
It was the eighth cycle in the Minor Leagues this season and the first by a Daytona player since Felix Pie accomplished the feat in 2004.
Jackson, the 31st overall pick by the Cubs in the 2009 Draft, finished a triple shy of the cycle while playing for the Class A Peoria Chiefs at Quad Cities last Aug. 16, but had never completed one or smacked a walk-off home run at any level.
"It's a pretty great feeling," Jackson said. "We've been playing well lately and we're almost back to .500, so it's a big win for the team."
Winners of five of their last six games, the Cubs are 30-32, seven games behind first-place Dunedin in the Class A Advanced Florida State League North Division.
After Lakeland jumped out to a 3-0 lead in the top of the first, the left-handed Jackson led off the home half of the frame with a triple to right field off right-hander Luke Putkonen, but the Cubs were unable to bring him home. The three-bagger moved him into a tie for third in the league with six triples.
The University of California product struck out in the third, then delivered a two-out RBI single in the fourth off Putkonen to give Daytona a 4-3 lead.
Facing lefty Tyler Conn to lead off the seventh, Jackson drove a double to left but was again stranded on the bases. The left-handed Jackson is hitting southpaws slightly better than right-handers this season -- he's batting .303 with a .539 slugging percentage against lefties and .285 with a .403 slugging mark off righties.
After the Flying Tigers tied the game, 4-4, with a run in the eighth, Jackson came up with two outs in the bottom of the inning with the bases loaded and left-hander Wilfredo Ramirez on the mound. He sent a long fly ball to the opposite field that Lakeland left fielder Brent Wyatt corralled on the warning track.
"When I hit it, I thought it had a chance, but I didn't get quite enough of it," Jackson said. "The wind had been blowing out [to left] pretty hard earlier in the game, but it had died down by then."
He got another chance to win the game with a man on first and one out in the 11th -- again facing Ramirez. With the winning run on first, he knew the Lakeland hurler couldn't get too fancy.
"I was looking for a fastball and I got one, middle-in," he recalled. "I was able to get the bat through it and hit it pretty hard."
There was no doubt about this one. It was Jackson's fourth homer of the season -- and second in three games. It also marked his sixth multiple-hit effort in his past eight games, and the three runs he drove in Monday night made 13 RBIs in his last seven outings.
"I was going through a tough slump there for a while, probably the toughest of my short career," said Jackson, who went 6-for-46 (.130) over 12 games between May 21 and June 2. "I've gotten a lot of help from the coaches and put in a lot of work trying to get out of it."
Marco Carrillo improved to 2-0 for the Cubs after tossing three scoreless frames. He gave up two hits and struck out four.