Ahead of the first meeting between the Reds and Carlisle in 33 years, we caught up with a man who played for both clubs.
Joining the Reds in October of 2001 - initially on loan from Sunderland - Chris Lumsdon made a terrific early impact for Barnsley.
He would go on to make 93 appearances, scoring 13 goals and was voted Player of the Year in his first campaign at Oakwell.
But it was with Tuesday night's upcoming opponents from Cumbria that the attacking midfielder really made his name.
He'd be forced in 2010 to retire through injury at 30-years-old but he remains involved with football, as he explained when we spoke ahead of the Carabao Cup tie this week.
“At the minute, I’m a qualified teacher and I’m a pundit for BBC Radio Cumbria." Lumsdon told us.
"I’m following the ups and downs of Carlisle. But I’m looking forward to coming down on Tuesday to Barnsley for the match.
“It’s funny really, but it will be the first time I’ve been back. Some of my mates go down to Oakwell once a year, they enjoy the town and the nightlife. It’s an annual thing for them. But yeah, this will be my first time and I’m looking forward to seeing the place again and hopefully watching a decent match.”
It's been a tough few years for Carlisle United who remain in League Two despite being one of the bigger clubs at the level, certainly historically.
As a pundit for local radio, there are few better to ask for an opinion on what's happening at Brunton Park.
“The club is going through a transition period. Our attendance in 2006 when I played my first game was 12,000 against Doncaster, whereas this year, for the first game of the season, it was just 4,800.
“When I was at Carlisle, we had an ambitious board that wanted to go up the leagues. We had just missed out on promotion to the Championship after going up from the Conference and League Two in successive seasons. It’s turned a little bit since then, but that’s football.”
But it was all so different when Chris joined the club in 2004.
Promotions, runners up in the Football League Trophy and a group of players who excited the Blues' fanbase on a regular basis.
It was a great time for the club, as Lumsdon explained: “The reason I signed for Carlisle was because when I came to look around, I could tell the club was good. It meant I could also move back to Newcastle and travel across, so it was perfect at the time for me.
“We hit the ground running straight away because we had players like Michael Bridges, Kieren Westwood, Danny Graham and Joe Garner. Players who’ve gone on to have really good careers.
“Looking back, we should have really gone up to the Championship that year, but we just ran out of steam in the end and got beaten by Leeds in the playoffs. Then, the lad who was running it, he gave the club away for a pound and they’ve kept it going since, but they’re in a bit of standstill at the minute.
“However, they’ve got a young squad now and it’s just a case of trying to rebuild again, try and get back on the up and up.”
So who are the players that Chris thinks we should keep an eye on when Steven Pressley brings his Carlisle side to Oakwell for Tuesday night's cup clash?
“They’ve just revamped the squad in fairness. They’ve signed a right-back called Christie Elliott, he’s a Geordie lad who looks very good. There’s also Nathan Thomas, who is on-loan from Sheffield United, he’s something else, he is really, really good on his day.
“However, they’ve also got some older heads like Byron Webster and [Nathaniel] Knight-Percival at the back, who both impressed last Saturday. They’ve been around at higher levels and should excel this season.”
Lumsdon's time at Oakwell - and perhaps his performances - are overshadowed by the turmoil that enveloped the club at that point.
The administration era is one that nobody remembers fondly but Chris spoke to us freely about how he saw it from the inside and still prefers to remember with fondness his years as a Barnsley player.
“It was fantastic for me at the age of 21 to come and get first team football at Barnsley. If I’m honest, getting relegated that year was tough, it hurt a lot. I felt as though me, Bruce Dyer, Gary Jones and Chris Morgan really pulled our weight but there were a few in that squad who let us down.
“Looking back at it now, we just needed one more win really. I still think about it to this day, the last-minute goals and the signings. So many players. I remember walking into the dressing room on my first day and the big names kept coming in and in. It was crazy really.
“However, the financial side collapsed in the end and a new takeover happened and we stopped getting paid. It was a shame because I really enjoyed my time at the club and living in the town. I won Players’ Player of the Year and Supporters’ Player of the Year in my first season.
“But there was a payment due to Sunderland if I played a certain amount of games and in the third tier and with all the financial stuff going on, that was me done. I couldn’t play. Which was tough really because there was interest in me from Championship clubs despite the relegation and I’d turned it down.
“But I ended up at Carlisle so I can't complain. I loved my football and it'll be great to see both my old sides go head-to-head this week."