In 1986, Gedman experienced three of the highlights of his career. Gedman was the battery-mate for Red Sox pitcher Roger Clemens on April 29 when Clemens struck out 20 batters in a game against the Seattle Mariners to set the major league single-game strikeout record in a nine-inning game. Gedman's 20 putouts during the game set the American League record for putouts by a catcher. On April 30, he had 16 putouts for a total of 36 in two days, which is the most for a catcher in two consecutive games. Gedman was also selected to the All-Star Game that year, to go with his appearance in the 1985 game. But the peak of his career coincided with one of its lows in the 1986 World Series. In the bottom of the tenth inning of Game 6, with the Sox leading by one run with two outs, Kevin Mitchell on third and Mookie Wilson at bat, reliever Bob Stanley threw a pitch that Gedman failed to handle. It was scored as a wild pitch, but many considered it a Gedman passed ball. Mitchell came in to score, tying the game. Then, Wilson hit a ball that went through first baseman Bill Buckner's legs to win the game for the Mets. The Sox went on to lose the deciding game, and the series.