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Heading into Season II the Bears were ready to forget about the upsetting Semifinals exit in Season 1. In Season II the league introduced a conference based system, the Legacy and Heritage Conferences spilt the league up and had teams fighting for their conference championship and a ticket to the World Series. The Bears were ready to take on the Legacy Conference.
A mediocre regular season had the Bears at an 8-7 record. Bears coach Robert O'Horan was embarrassed that the team went from an undefeated regular season to a team just over .500. The one bright side to the season was completing the season sweep of the Genovese Knights 3 games to 0 and taking home the Battle of the Bosses Cap for a second consecutive year. Despite the subpar play the Bears were third place in the Legacy Conference and got a ticket to the playoffs.
To kickoff the Quarterfinals the team was ready to take on Drink Joe. In a No.2 vs No.3 matchup the No.3 Bears pitchers shutout the Joe and booked a trip to the Semifinals for the second season in a row winning 1-0. In the Semifinals the Bears were met with the No.1 team in the Legacy Conference the Pandya Superkings. Yet again Bears pitching helped the team with back to back shutouts and sending the Bears to the World Series with another 1-0 win. The team didn’t quite get the same pitching in the World Series as they had in the first two rounds of the playoffs. Eireannia ended up losing the World Series game to the Idno Crimson Dragons 2-0. Coach Robert O'Horan said in the postgame interview that “Although losing in the World Series sucks we still made it as far as we could. We had a not so great regular season and the boys turned it around when it came to the playoffs”
Yet again the Bears added some silverware to the teams trophy case, adding a Legacy Conference Championship, the Battle of the Bosses Cap and a World Series Runner-up medal.
