Yankees Trivia (from Cary Greene)

June 2026

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For the Tuesday Discussion this week we asked our writers to share their favorite Yankees trivia question. WE then decided to space these out rather than putting them all in one post.

Here is another bit of trivia, this time from Cary Greene:

Q: In the regular season, the biggest Yankees comeback wins in franchise history were from 9-run deficits. How many times have they accomplished this feat and - can you recall the games?

A1: Most recently, on May 16, 2006, when they rallied from down 10-1 to defeat the Rangers 14-13. The game, which featured a 3-run home run in the bottom of the 6th-inning by Derek Jeter, was sealed with a walk-off, two-run home run by Jorge Posada, who drove in Johnny Damon on the blast as well!

A2: On August 25th, 1987, Roger Clemens faced off against Tommy John in a game that promised to be a pitching duel, but that of course never materialized, as the Yankees were down 9-0 going into the bottom of the third-inning. After Dave Winfield launched a three-run homer, the Yankees played classic "next man up" baseball and they drew to 9-8 when Don Mattingly doubled in Willie Randolph. Then, Dave Winfield came back up to drive Randolph in with a single and with that, the Yankees had tied the ballgame, but they weren't done in what would become a historic bottom of the third-inning. The Yankees added two more runs on a wild pitch and a passed ball and they found themselves up 11-9, in a game they eventually went on to win 12-11 on a Wayne Tolleson single in the bottom of the 10th. 

A3: On June 26, 1986 at Yankee stadium, Boston chased Yankees starting pitcher Ron Guidry early and built a commanding 9-0 advantage by the top of the second inning. Boston starter Roger Clemens was on the mound and he was cruising, but the Yankees slowly started chipping away at the lead and in the bottom of the 10th-inning, Mike Pagliarulo got things started with a walk. Rick Cerone then sacrifice bunted Pags into scoring position and Wayne Tolleson singled him home for a 12-11 win

A4: On May 27th, way back in 1933, the Yankees trailed the Cleveland Indians 11-2, but they rallied to score 12 runs in the bottom of the 8th-inning, but the Bronx Bombers rallied back to tie the score in the 8th-inning, but they weren't done yet. With the bases loaded, Bill Dickey swatted a grand slam, driving in Lou Gehrig, Ben Chapman and Tony Lazzeri and the Yankees closed it out in the top of the 9th behind Herb Pennock, who earned his second save of the season.