The Gloucestershire County League side took the lead early on through Josh Stokes but Tom Hutton equalised soon after. Jamie Evans and Ryan Mudd scored either side of half time to put Kingswood 3-1 up and a late Ali Bamford header proved nothing more than a consolation for the Western League side.
The O's went into the match having halted a run of form that had seen only one win in eleven games, that being a narrow win over Cheltenham Civil Service in the second round of this competition. In comparison, Kingswood suffered a heavy 6-0 league defeat to Frampton United last time out but would still have felt confident taking on a side just one division above them.
Oldland were on the back foot right from the word go as keeper George Dempsey was yellow carded inside thirty seconds after a handball outside the box. And worse was to follow when Josh Stokes slammed home from close range on six minutes to give his side the lead. Cory Pring was left in space to head over the bar on ten minutes and Ben Foxwell's attempted lob over Dempsey lacked height and was easily caught by the keeper.
Good work from David Stone found some space inside the box and his ball back across goal was thumped home by Tom Hutton for his first goal of the campaign on 21 minutes. It should have spurred the O's on to grasp the game and kick on but aside from a Josh Dempsey header and a Ryan Dunn shot that both went over, chances were at a minimum. And Kingswood made their opponents pay on 42 minutes when Jamie Evans broke the offisde trap and slotted coolly past Dempsey and into the net.
Stone then had a chance to level early in the second half but his flicked shot was gratefully grabbed by Paul Eldridge in the Kingswood goal. He then saved well from Hutton's volley, pushing it away for a corner. It seemed like an Oldland equaliser was inevitable but on 54 minutes, a poor clearance was seized upon by Kingswood and Ryan Mudd finished through the keeper's legs to make it 3-1.
The rest of the second half saw Oldland push to get back into the game but lacking the final clinical touch and a stroke of luck. Hutton's curling free kick was tipped over for a corner, Lewis Parker's shot went past the far post, Hutton then almost scored direct from a corner before Gary Shorney's shot was superbly saved by Eldridge. Late on, both Ali Bamford and Dunn hit the crossbar before two minutes into stoppage time, a corner was headed home by Ali Bamford despite a gallant effort from a Kingswood defender to keep it out. It was too little, too late though and Kingswood progress into the fourth round.