A hat trick from Louis Grant, alongside goals from Liam Dickens, Jack Barlow and Lawrence Heward saw off the North Yorkshire side.
The Owls made just one change from their 3-0 midweek defeat to Bridlington Town bringing back in club captain Darren Hanslip with Jack Richardson moving to the bench.
Before kick-off the teams lined up in an unfamiliar set-up with the pre-match photograph being with the teams mixed up. This was in commemoration of the 1914 Christmas Truce.
Pickering kicked the game off and immediately went in search of the opening goal. Neat play between Ryan Cooper and Billy Logan set the latter free in on goal with just Damian Steer to beat. However, Steer stood strong and Logan could only fire his shot straight at the shot stopper much to the angst of the home fans.
Just seconds later, Pickering had another chance, this time it was Joel Ramm who was only inches away from opening the scoring. The ball dropped onto his right foot just outside the area but his volley dropped just wide of the right hand side post.
The Pikes continued to press forward, giving the Owls little chance to get ahold of the ball and to play in wide areas like they are accustomed to. The pressure continued from Pickering though, frustrating not only the Owls with their impressive forward play but themselves as well with both Ramm and Joe Danby being caught offside on more than one occasions as they looked to break the back line of the Owls defence.
With the Owls struggling to create any chance in the opening 15 minutes, it was winger Jonathan Oglesby who took matters into his own hands. He took ahold of the ball 25 yards out and unleashed a rasping effort on goal which whistled just inches over the bar.
This gave the Owls some impetuous as just 30 seconds later leading scorer Marc Cooper wasted a guilt edge chance as Grant and Alex Flett linked well to set up Cooper but he could only fire over the bar with just Toby Wells to beat in the Pickering goal.
At the other end, the Owls where fortunate to keep out Logan as Steer misjudged a free kick which was played in from the left. His punch was very short, but Logan could not find room to muster a shot and the ball was ushered out of play for a goal kick.
Only 60 seconds later, in the 20th minute, Logan really should of made it 1-0 to Pickering but he could not capitalise on a Dickens slip and as he raced clean through on goal the ball seemed to bobble just as he was about to pull the trigger and the ball trickled wide of the mark.
The Owls seemed to be getting a foot in in the game as the chances kept coming for them. Firstly, Hanslip tired an audacious overhead kick from outside the box but it went wide of the mark. Then, Hanslip dragged a shot wide after Cooper bumfuzzled his was past two defenders, squared the ball to Grant who laid it off to Hanslip but he could not find the back of the net.
Chances kept arising for the visitors as Dickens floated the ball into the box, Hanslip saw the Brody Robertson was making a run behind him and dummied his header but Robertson could not latch onto the ball with the goal gaping.
Fortunes changed soon after in the 38th minute though. Oglesby pounced on a long ball forward by right back Luke Mascall but as he rounded the keeper he was upended and a penalty was awarded. Not only that, but Wells was sent off for denying a goal scoring opportunity.
Just four minutes later, Grant nearly had his second of the game but a low cross by Robertson caught the heel of the striker and it spun wide of the keepers left hand post.
With the Owls having a man advantage, they looked to exploit this by moving the ball around and using long balls over the top to break their high defensive line.
As the clocked ticked into injury time a corner was won on the right hand side for the Owls. Oglesby swung the corner in, and Dickens headed it home at the far post much to the delight of the travelling support. The referee blew his whistle moments later to signal the end of the half.
The Owls started the second half off as the first half had ended, creating chances and generally spreading the ball around effectively. It was only three minutes into the half when the first chance came. A corner from the right was headed goal bound by Hanslip but the keeper held the header well.
With the Owls on the ascendency, it was Cooper next to have a shot on goal as he took the ball past two defenders but he could only shoot wide of the mark from just outside the box.
It was not long though until the ball was in the back of the net. Oglesby won a strong challenge on the right wing; he then played a delightful ball with the outside of his boot into the channel where Grant was to coolly dispatch his second goal of the game.
With the Owls having an unassailable lead against 10 men you would think Pickering would struggle to create chance. However, Pickering did find a way back into the game only four minutes later. Logan chased a long ball forward and as Steer was back peddling after deciding not to come for the ball, he delightfully chipped the ball home into the net.
Only seven minutes later and the three goal cushion was restored as Grant made sure of his hat trick with a deft 25 yard curler into the top corner. It was a goal right out the top drawer and as he peeled away to celebrate, the management team signaled that he was to be replaced by Heward.
As the Owls did just 15 minutes before, they let slip the three-goal cushion, as Logan was on hand again to score past Steer. This time he drilled a free kick in from 20 yards through Steer much to his annoyance.
Once again, this only lasted three minutes as Barlow netted for the Owls after a Cooper through ball was played to perfection. The striker had the easiest of finishes past the unaccustomed keeper.
The scoring was finally complete when Heward smashed the ball home in at the right end. He is used to scoring at the wrong end with his formidable record this season but he now has his second of the season much to his delight.
This win for the Owls lifts them to ninth in the table with games in hand over every team above them. The Owls next game is on Tuesday as they travel to Tadcaster Albion, with a 7:45pm kick-off.
Their next home game is on Saturday against Athersley Recreation at the Bradley Community Stadium, with a 3pm kick-off.