The heavy rain that had battered north Edinburgh in the lead-up to the match abated by kick-off to the delight of the 200 or so supporters dotted around the perimeter of the pitch.
Trialists Kanayo Megwa and Sanmi Oluwaseun were both handed starts with Josh Currie, Yrick Gallantes, and Oscar MacIntyre not involved.
Hibs looked lively against a Strollers side featuring a mix of youth and experience and a fair number of trialists, and Robbie Hamilton put them in front from close range with six minutes on the clock.
Ethan Laidlaw then went close to doubling Hibs’ advantage as he cut in from the left but his low shot shaved the far post as the visitors took control in the early stages.
Hamilton then sent an effort just over the bar as the wee Hibees remained camped in and around Strollers’ penalty area but Gary Jardine’s side nearly levelled on 17 minutes against the run of play.
Alieau Faye was sent clean through on goal and although his low shot evaded the diving Murray Johnson, the Frenchman’s effort smacked the base of the post with Johnson smothering the rebound.
The goalkeeper was then called into action moments later, getting down well to push away a fierce shot as Strollers began to find their rhythm.
At the other end, Hibs still looked dangerous on the break and Murray Aiken had a shot saved before O’Connor netted his first, firing the ball into the roof of the net from inside the six-yard box.
The visitors continued to push for a third goal without creating any clear-cut chances and Strollers took advantage, Lewis Duffy reducing the deficit just before the interval after Hibs had failed to clear a corner.
Hibs hit back straight away with Aiken tapping home following a mix-up in the Strollers defence.
Eddie May and Gareth Evans made one change at the interval, replacing Johnson with a trialist goalkeeper as well as tweaking the shape.
The second half had barely begun before Hibs increased their lead. O’Connor was upended after a surging run into the box and he dusted himself down to send Mac Whyte the wrong way from the penalty spot for his second and Hibs’ fourth.
Losing a goal so early after the restart seemed to jolt Strollers into life and the Lowland League side’s attackers began testing the substitute goalkeeper, who had to be alert to push a dangerous ball out for a corner.
Hibs still looked dangerous on the counter attack but on 65 minutes Strollers scored again, Faye converting from the penalty spot, and minutes later they scored again with a speculative effort from Andrew Johnston.
With the hosts pushing for an equaliser, Hibs shifted up a gear and with ten minutes remaining, O’Connor notched his third as he outpaced the Strollers defence before slotting the ball just inside the post to secure a 5-3 victory for the wee Hibees.
Hibs are next in action on Tuesday, July 6 when they take on Dunbar United at New Countess Park.
Hibs: Johnson, Megwa, Leddie, Blaney, Fairley; Aiken, Trialist, Oluwaseun, Laidlaw, Hamilton, O’Connor. Subs: Trialist GK, Fordyce, Lawson, Molotnikov