Goals from defenders Luke Crewe and Asa White in the second half made the O's pay the price for missing several chances before half time.
O's were still short of several players due to holiday commitments and once more, numbers dictated that keeper Josh Dempsey played outfield with reserve gloveman Lionel Fear deputising between the sticks. Elsewhere, Connor Davies was suspended and Ashley Bernard, Ryan Dunn and Lewis Parker were all missing from the squad list.
Fear had to save sharply from an early Hengrove attack and from the counter, Tom Kngton in the visitors goal pulled off a smart parry to deny Tom Morgan. It was Morgan who had the lion's share of the chances before the interval but saw one shot cannon off a defender's head, another pushed round his post by Kington and a third curl well wide from a tight angle.
Hengrove, fourth in the pre-match table, had been identified by boss Dale Dempsey as a difficult opponent in his programme notes but their chances early on aside, they didn't threaten the Oldland goal too much although Billy Vaughan did shoot wide from distance.
Five minutes after half time, Oldland were given a massive let off not once but twice. A ball into the box was headed on to the crossbar by Luke Crewe and Vaughan completely shanked his shot with the goal gaping. The goal sparked Oldland into life and Morgan curled a shot over before Josh Williams rifled a shot into the side netting after a super reverse pass from Matt Curnock.
Just before the hour mark, Hengrove took the lead when an inswinging corner came off the back post, a shot was just kept out by Fear before Crewe finished from close range.
The greens then went two up on seventy minutes. Vaughan's free kick was spilled by Fear into the path of Asa White who netted from inside the penalty area.
Craig White's fierce free kick deflected off the wall for a corner shortly afterwards and as time ticked towards the final moments, Owen McCallum came on for his Toolstation debut at the age of just sixteen joining fellow teens Calum Winstone, Josh Williams and Matt Curnock on the field.