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After a lackluster month of May caused the Yankees to slide into second place, chasing the eternally-hated Boston Red Sox , the ‘99 Yanks had a prime opportunity to close the gap with a three-game set with their rivals in the Bronx. A loss in the first game and a win in the second, however, set the stage for a critical rubber match in which the Yankees could either cut their deficit to just half a game — or finish the series in a worse spot than they started. Fortunately for the Yankees, they had on the mound a pitcher who had troubled them for years while wearing a Boston jersey: Roger Clemens.

While the Rocket had not been his old Cy Young self during the beginning of his pinstriped tenure, on that day, he reminded the world why he was a first-ballot Hall of Fame talent. May 27: Yankees 4, Red Sox 1 ( box score ) Record: 26-19 (2nd, 0.5 GB) On paper, the Yankees had the edge in the pitching matchup, and it wasn’t even close.



They were sending out Clemens, a 16-year veteran, five-time Cy Young winner (including the previous two seasons), the 1986 AL MVP, and who entered the season with 233 wins and 44 shutouts to his name. The Red Sox, meanwhile, countered with Pat Rapp, a six-year veteran who was on the fourth team of his career and who entered the season with a career 4.52 ERA.

And so, naturally, we ended up with a pitchers duel. Nobody reached scoring position until Scott Brosius doubled with two outs in the bottom of the third, and Rapp proceeded to get Derek Jeter.

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