[1] As a junior in 2019, Winn had a 13–0 record on the mound with a 0.67 ERA and 117 strikeouts over 76+1⁄3 innings pitched while also hitting .417 with eight home runs and 46 RBIs, earning the title of District 22-6A MVP.

[8] After slashing .262/.370/.388 with three home runs, 34 RBIs, 15 doubles, three triples, and 16 stolen bases over 61 games, he was promoted to the Peoria Chiefs of the High-A Central in late July.

[11] After hitting .349/.404/.566 with one home run, 15 RBIs, and 15 stolen bases over 33 games, he was promoted to the Springfield Cardinals of the Double-A Texas League.

[14] His season totals over 119 games between both teams included a .283 batting average, 12 home runs, 63 RBIs, 36 doubles, and 43 stolen bases.

[20][21] He was inserted into the lineup that evening, making a diving play on a ground ball in the second inning and getting his first hit, an infield single, going 1-for-4 in his first game.