After all, it is only a couple of years since the 25-year-old Donny midfielder was standing in their shoes.
Bailey, a product of the Newcastle youth system, was playing for Gateshead in 202122 when the National League North side battled through four rounds and two replays to secure a glamour tie against Charlton at the International Stadium.
Though the Addicks triumphed 2-0 on Tyneside, they were under siege for lengthy stretches of the contest and Bailey is expecting a similar challenge against the Southern Premier Central leaders, who stunned League One Northampton in the first round.
"I remember exactly how I felt going into that game," says Bailey, whose team-mates that day included current Millwall striker Macaulay Langstaff.
"You want to show that you can do it at that level and show you can mix it with the players that are in a higher league. We did that, and I think the boost that gave us and that confidence we gained was actually really important in us winning the league that year. It was like 'Okay, we really are a good team'.
"So, yeah, I know there'll be a lot of lads playing for Kettering who've got a point to prove and who want to make a mark.
Incentive
"But in the same breath, we're kind of in the same boat.
We also want to prove ourselves against the best and if we get through this then we might have an opportunity to play one of the biggest teams in the world.
Denne historien er fra December 01, 2024-utgaven av The Football League Paper.
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Denne historien er fra December 01, 2024-utgaven av The Football League Paper.
Start din 7-dagers gratis prøveperiode på Magzter GOLD for å få tilgang til tusenvis av utvalgte premiumhistorier og 9000+ magasiner og aviser.
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I'd still want to keep Pat on side
Patrick Bamford has always been a player who divides opinion amongst Leeds supporters.
WHITES & THE BLADES SPEED ON
LEEDS and Sheffield United maintained their pace at the top of the table with comfortable home victories - but Sunderland slipped off the summit.
BAILEY: WE'LL GIVE POPPIES THE RESPECT THEY DESERVE
OWEN Bailey knows exactly how pumped up seventh-tier Kettering Town will be when Doncaster Rovers roll into ramshackle Latimer Park today.
TOWN EARN THEIR CORN!
HARROGATE mon Weaver breathed a sigh of relief after his side edged past Gainsborough Trinity at a rain-sodden Exercise Stadium.
OH MY JOSH - O'S KEEPER IS THE HERO!
RICHIE Wellens praised keeper Josh Keeley as Leyton Orient reached the third round following a dramatic win over National League Oldham.
'IT HASN'T BEEN MY WHOLE FOCUS AND THAT HELPED ME
SHAUN Barker never attempted to conceal the fact that he had no burning desire to play football.
MATT'S BOYS SHOW CLASS
WYCOMBE side-stepped a tricky second round fixture by defeating Wealdstone at Grosvenor Vale.
LUKE SEETHES OVER SLOPPY SWANS START
LUKE Williams admitted he gave his players the hairdryer treatment at half-time after seeing them come into the break trailing against bottom of the table Portsmouth.
UPSET FOR HARRIS AS TYLER HITS STUNNER
Neil Harris insisted the fact that Millwall were bitterly disappointed to claim only a point shows the progress his side have made over the past 10 months.
ANTE AT THE DOUBLE FOR ON-SONG CITY
NORWICH head coach Johannes Hoff Thorup paid tribute to the home fans after watching his side come through a tough test against Luton to win comfortably in the end.