Gaylord Perry was a formidable pitcher up until the end of his career, so it should come as little surprise that the right-handed hurler surpassed the 300-wins mark. His 300th victory came when he was 43-years-old and took down the New York Yankees, 7-3. Perry had four strikeouts during this iconic and memorable game, making him just the 15th pitcher in MLB history to reach 300 career wins.