The Northern Irishman kicked off the evening session on day one against Woollaston and had to come from behind to advance.
Allen got the first real chance but could only make nine and coughed up a simple opener for his opponent approaching the halfway mark.
But Woollaston saw his break end on 15 and Allen made him pay, potting a stunning red to get back among the balls en route to a 52-15 win.
“It’s just chaos every year, no matter how many times you keep coming back here it just doesn’t get any easier,” Allen said.
“You feel like you’ve lost, you feel like you’ve won, and you just never know where you stand.”
The Northern Irishman added: “That’s part and parcel of the competition. It is chaotic, it is manic, it does weird things with your brain, but that’s why we all keep coming back.
“It’s a complete lottery but it is a lot of fun and you have to treat it for what it is.”
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Funny moment as Bingham offers to give glasses to fan after missed red
Wales’ Michael White, the 2015 Shoot Out champion, entered the Swansea Arena next to take on Mohamed Ibrahim.
There were some signs of nerves from both men until White made a brilliant break of 92 to ease through.
The all-English clash between Oliver Brown and Allan Taylor was an edgy affair. Both missed a raft of chances, but it was Brown who prevailed after recovering from 20 points behind to win 35-33.
Up next, Xing Zihao pulled off some exceptional shots to establish a 30-point lead, but it was Xu Si who timed his comeback to perfection to advance to the round of 64 courtesy of a 42-31 victory.
Mark Davis made a 50 to grab the early initiative against reigning world women’s snooker champion Baipat Siripaporn and eventually triumphed 94-8.
A frantic finish in the contest between Manasawin Phetmalaikul and Mostafa Dorgham saw the former come up a point short as he raced round the table before being timed out.
After that tight affair, Cao Yupeng turned in a dominant display to beat Sydney Wilson 73-32.
Rory Thor’s encounter with David Gilbert was a proper advert for Shoot Out snooker, as both players saw several opportunities come and go during a chaotic 10 minutes. Malaysia’s Thor got in first and let a gilt-edged chance slip with a few minutes left, allowing Gilbert to progress.
Fan favourite Dominic Dale then put on a late show for the fans as he chased an unlikely century with the seconds ticking away. A miss on the pink ended his break but he will be back in the next round after beating Fan Zhengyi 64-1. ‘The Spaceman’ even treated those in attendance to a victory song.
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Dale celebrates Shoot Out victory with a song
Following that act, Duane Jones made light work Jenson Kendrick, easing to a comfortable 82-0 win.
Joe O’Connor was in command in the next match but gave Andy Lee a glimmer of hope when he failed to hit a cushion and offered up a chance with ball in hand. Lee failed to capitalise, though, and the Englishman sailed through to the next round.
Kyren Wilson then survived a scare against Daniel Wells. The five-time ranking event winner gifted his opponent a chance to launch a late attack but Wells was timed out before he could pull off the comeback.
The break of the day perhaps came from Louis Heathcote, who looked down and out against Xiao Guodong until he hit back to seal a 45-43 win, potting the final blue with seconds to spare.
England’s David Pullen beat Yuan Sijun in a one-sided contest before his compatriot Ian Burns joined him in the last 64 after a comfortable victory over Florian Nuessle.
The final match of a marathon day was the highly-anticipated clash between Jimmy White and Zak Surety. White looked nervy throughout but put himself in with a shout of a comeback victory before twitching on the final blue with the frame at his mercy to lose 62-43.
