With the Cubs’ win over the Pirates on Wednesday, that unfortunately closes out the season against them. For 2008, the Cubs were 14-4 against Pittsburgh.
To look for a season when the Cubs won that many games in one season against one team, you would have to go back to 1978. Under the helm of manager Herman Franks, Chicago had a losing season record of 79-83 good for third place. Despite the losing record, they managed to win 15 against NL East rival St Louis Cardinals.
Winning 14 against the last place Pirates may not seem like such a big deal but consider this… The Cubs were 14-16 against them for the last two seasons (2006-2007).