Conversation so far:
When did Clemens play with the Red Sox?
1986.
How did he perform during the 1986 season?
The 1986 ALCS clincher was Clemens' first postseason career victory.
He did not win his second until 13 years later.

Question: Did he play in the world series?
Self-contained rewrite: Did Roger Clemens play in the world series?