First time I did it, the OL team won 103 (and the WS) and the CL team won 81 (and the WS).
Second time I did it, the OL team won 102 (and the WS) and the CL team won 88 (missed the playoffs when we lost the play-in game).
I feel lucky to have won a WS in a CL (especially with a .500 team). Most of the owners in there really know what they're doing in OL-style leagues.