The Stark’s Park boss has been cruelly denied a cup final appearance three times previously in his managerial career; leading Hearts and Livingston to cup finals only to be sacked before the games were played, and then Rovers’ chance of playing in the Challenge Cup Final in 2019/20 was called off due to the Covid-19 pandemic.
Midfielder Matthews says that if McGlynn finally got his hands on some cup silverware it would be richly deserved.
"It would be big for everyone but I think it would be pretty special for the gaffer to win a trophy here,” he said.
"He's been here for ages and the fans love him and all the players appreciate him as well.
"He's been massive for me since he's been here. I've improved massively under him.
It would be great for him and Smudger [assistant boss, Paul Smith] to win a trophy for the club, though Smudger has already won this trophy.
"It was him and Grant Murray who won it against Rangers in 2014 when he was here so he could potentially add a second Challenge Cup to his record.
"It's a bit of coincidence with Grant Murray being there [as Queen of the South’s assistant boss]. "He was my first manager here. He was great for me. He was the one who picked me up from the youth academy.
"Him and [then first team coach] Laurie Ellis used to take the reserve games. I owe a lot to him. I learned a lot in my first year under him and Laurie.
"He let me train with the first team, though he was quite strict about the jobs away from football.
"I hated it at the time, but that's probably another thing you don't realise that will stand you in good stead.
"When we were ground staff we used to come back here every day and clean stuff even if it hadn't been used!
"I used to clean the stand on a Monday after the games and then again on a Saturday.
"That was all thanks to Grant and Laurie!”
Matthews himself was at the club when they last won the trophy – then called the Ramsdens Cup – with a famous win over Rangers in 2014 and says it’s an occasion he remembers well- and hopes to relicate.
He says: "I was there but I wasn't part of the squad so I feel a bit stupid saying I was part of it.
"I took part in the photos and the celebrations afterwards though!
"I was in the stand watching the game. It was my first year at Raith. I was 17 at the time. It was me, Lewis Vaughan and David Bates, all just in the squad, watching it.
"It was pretty special that day.
"I probably didn't realise how big of a thing it was until I saw the reaction of the fans and the celebrations afterwards.
"When you're young you just take things for granted. Because that was my first season and they got into a cup final I was probably thinking that my chance would come soon.
"Of course, that was against Rangers so it was massive, but for us this is probably the most realistic chance we have of winning a trophy.
"It doesn't come often. In my nine-year career so far this is my first chance so hopefully we can take it.
"I won League One with this club but it wasn't quite the same. We didn't get the chance to lift the trophy and celebrate with the fans.
"You can't take anything for granted.
“The club has only ever won three trophies I think, so that just shows this isn't something that happens every season.
"We have to take advantage of it.
"Everyone is looking forward to Sunday. Hopefully we get a good week's training in.
"I've been at this club for ages now, I've been here nine years, and this will be my first time playing in a cup final.”
The 26-year-old was handed the captain’s armband for last Saturday's 3-3 draw at Arbroath and, with captain Kyle Benedictus suspended and vice-captain Christophe Berra rated doubtful due to injury, he could find himself leading the team out at the Excelsior Stadium on Sunday.
He says it would be a massive honour.
"That was my first time [as team captain] in a league match. I was captain against Cowdenbeath in the League Cup, but that was a special moment on Saturday.
"Obviously I was disappointed we couldn't win the game but I've been at this club for so long now it was a privilege to wear the armband.
"I don't know if I’ll be captain this weekend. I've still to find that out.
"If it did come to it I'd be buzzing if I was!
"I'm really excited and I'm sure everyone else is.”