Oldland lost in the first game under Jon Toy in a midweek floodlit match at Chipping Sodbury.
The game was level at the break but Jordan Chubb continued his recent good form to put the visitors ahead on 47 minutes. The lead did not last long however as an unfortunate Don Solomon own goal brought Sodbury level.
There were no further goals and, in accordance with this season's Les Phillips Cup rules, the match went straight to penalties. Oldland could not match Sodburys efforts and so depart the cup at the first attempt.
All eyes now turn to Saturday's home league game against Bishops Lydeard.
Team selection has not been published for this fixture yet.