Reyes had gone 28 starts since he last won on June 13, 2008 pitching for Atlanta, but he ended his drought in style, the Blue Jays beating Cleveland 11-1 in Reyes' first complete game.
The home fans chanted Reyes' name while jubilant team mates rushed the 26-year-old pitcher in celebration.
"It was exciting. Couldn't be a better game to do it," Reyes told reporters. "This team is awesome. They wanted to see me break the streak as much as everyone else."
The long-awaited win for the left-hander allowed him to escape being the first pitcher to go 29 starts without a win. He had tied Matt Keough (1978-1979) and Cliff Curtis (1910-1911) for the mark of 28 in a row.
Reyes allowed the one run and eight hits over the nine innings on Monday.
(Writing by Jahmal Corner in Los Angeles; Editing by Peter Rutherford)