As a teenager, Conway played for local Lowell teams. In 1884, he played outfield for the Salem team in the Massachusetts State Association, and pitched for the Lawrence team of the New England League in 1885.\n', '

Conway was 21 years old when he entered the majors in 1886 with the Baltimore Orioles, playing for them one year before joining the Boston Beaneaters (1887–1888). While playing for Baltimore, Conway entered in the baseball record books when he made battery with his older brother, Bill Conway, to form one of 16 pitcher/catcher combinations of brothers in major league history. His most productive season came in 1887, when he collected career-numbers in wins (9), starts (26), and innings pitched (222 ⅓).\n', '

In a three-season career, Conway posted a 15–24 record with a 4.78 ERA in 41 appearances, including 41 starts and 39 complete games, giving up 187 earned runs on 404 hits and 137 walks while striking out 121 in 352.0 innings of work. He also played 18 games as an outfielder, compiling a career .230 batting average (47-for-204) with 27 runs and 14 RBI.\n', '

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