The draw for the first and second round of the competition was conducted this afternoon at Hampden Stadium, pitting the young Gers against Bo’ness United at home before a trip to Clyde awaits the winners.
And Webster, who spent last season in the Lowland League on a season-long loan with Cumbernauld Colts, says he’s well aware of what’s required to meet the physical and tactical demands of the competition.
Speaking to RangersTV, the 19-year-old defender said: “It will be a good draw. I played against them last season for my loan club and they were good.
“They started the season well, had a stint in the middle where they weren’t so great, before they brought it back up. They will be a tough side to play against.
“I relish it a lot because it improves my game playing against men, and, by having that experience of playing 25 games for Cumbernauld Colts, I can use my knowledge and help the other boys out as well.
Last season marked a first loan in senior football for the teenager, who is the son of former Gers defender Andy Webster.
And it was a positive season on both an individual and collective level for the defender, who made just under 30 appearances for the side in a campaign where they finished fourth in the table.
Webster insists he’s better for the experience of sampling a senior environment, and he hopes that he showcase his development on the pitch for Gers B this term and when opportunities to train with the first-team arise.
He added: “I really enjoyed it. It was a good place to go and the staff were really good. The backroom staff are very friendly and inviting; my teammates were a good bunch of boys.
“It was a big accomplishment for the club to come fourth, and even how far we got in some of the cup competitions. The experience that it gave me was second to none.
“It was daunting at first, and the first couple of training sessions were a little nerve wracking because I had never experienced something like that before.
“But once I got comfortable in the environment, I was able to blossom and enjoy having a laugh with the boys.
“I feel that I’ve gained so much new knowledge from playing for Colts, and hopefully that can rub off on some of the boys here.
“I feel like my communication has improved with the people infront of me, as well as my power to jump ahead of players.
“As a defender you can see the full game before everyone else. If there’s a midfielder playing off the shoulder, for example, you need to be able to talk to the players ahead.
“You dictate through your voice, so it’s very important to have good communication skills.
“The first-team here is a lot higher quality, but at the same time you take aspects from the Lowland League because, at the end of the day, they are seasoned professionals round at the first-team.
“You need to be able to handle yourself properly and be ready for it.
“I want to keep improving as a player and become more of a leading figure. It’s important that I guide the younger players coming up and help us as a team.”