Tim,
You need to get yourself the CD-Rom of the game.

In this version of the game, the manager strategy of Base Running has an effect on the scenario you present.
In the CD-Rom game, in-game managing allows you to make the decision on whether you try to run for the extra base or not and send a trailing runner or not, and for the defensive team to throw for the lead runner or trailing runner.
Thus, with the max rule setting of "allowing for throwing errors," which the Online version has selected, there is the opportunity for the OF to receive an error in this fashion - even off the hitter's card.