The Owls Under-18s reached the fourth round of the FA Youth Cup after beating Hemel Hempstead 5-4 on penalties.
The game was 1-1 after 90 minutes, during which Devlan Moses’ opener was cancelled out by George Still.
The visitors took the lead in extra time with Noah Harvey on target, but a last-minute header from Dom Weston sent the match to penalties.
Wednesday were the first to carve an opening when Reece Johnson had a shot blocked after weaving his way to the edge of the six-yard box.
Then, Carlos Rodrigues crossed to Moses but the forward couldn’t adjust his feet to strike cleanly.
Hemel came close to opening the scoring when Brad Smith had two shots blocked from close range.
The combination of Rodrigues and Moses linked up again with the latter meeting the former’s cross from the right but his effort cleared the crossbar.
Northern Ireland youth international Moses had a busy half and went close again moments later, driving forward to the left of the Hemel area before drilling a low shot across goal that dragged narrowly wide of the far post.
But the forward was not to be denied and scored with his next opportunity.
It was a carbon copy of the chance moments earlier, but this time the striker smashed beneath Hemel goalkeeper James Taylor’s crossbar to put the Owls in front.
The visitors were unfazed after going behind and continued to search for a goal of their own, which arrived following a flurry of set pieces with five minutes of the first half remaining.
Phillips tipped over a curling Still free kick from range, the resulting corner was nodded behind and the away side found the net with the next dead ball.
It was Still once again with a bending, deep corner which nestled inside the far post to restore parity.
After the restart, Bruno Fernandes tried his luck from 25 yards but the strike drifted over the top.
Smith was inches away from putting Hemel in front, but Joe Emery was well-positioned to clear off the line.
Smith came close again seconds later, nodding a deep cross just wide of the upright.
Hemel continued to pose a threat with another quick breakaway that ended with captain Brad Roberts going close from 20 yards.
The two sides could not be separated after 90 minutes and the game went to extra time.
Sam Hejjaha fired over from the left flank as Hemel continued to carve out the majority of the chances, and they went in front in the second period.
A deep corner was headed across goal, where Harvey was finely poised to smash high into the Owls’ net.
As the clock ticked down it seemed the hosts had run out of time, but as Wednesday poured bodies into the box for a last-minute corner, the ball fell to Weston whose header levelled the scores.
And so the contest went to penalties.
Goalscorer Still stepped up first but saw his attempt fly high over the crossbar.
Every other penalty was dispatched, with Tyrell Dawes netting the decisive spot-kick for the Owls to set up a tie with Reading at home in round four.
Wednesday | Phillips, Rodrigues, Dawes, Kakay (Hunt 98), Swales, Emery (Shaw 103), Mbaya (Weston 67), Thornton, Moses, Fernandes, Johnson