After receiving a warm reception from Dundalk supporters recently, former Lilywhites hero Dane Massey is now hoping to break their hearts on Friday night when his Bray Wanderers side entertain Stephen O’Donnell’s men in the second round of the Sports Direct Men’s FAI Cup

Massey, who made 291 appearances for Dundalk between 2013 and 2020, picking up 14 major honours, was back on his old stomping ground recently to provide co-commentary for Dundalk’s UEFA Europa Conference League tie with KA Akureyri.

It gave the 35-year-old, who returned to Bray Wanderers at the start of the season, an opportunity to get a first-hand look at Stephen O’Donnell’s men ahead of Friday’s cup tie, which represents Dundalk’s first trip to Wicklow since 2018.

Bray currently lie sixth in the First Division and Massey, who has scored in the Seagulls’ last two league games, said he was under no illusions about the difficulty facing Ian Ryan’s side on Friday night.

“I had to laugh when the draw was made,” he said after the game with KA. “I’d like to say Dundalk will struggle but with the class and quality they have, it’s going to be an extremely difficult game for us.

“We have a very young squad with a good young manager at Bray so it’ll be a good test for us and when you look at the competition; Shamrock Rovers are out, Pat’s and Derry have each other in the second round, so maybe it’s maybe a chance for one of the lesser clubs to go and maybe get to the final this year.”

Massey won the FAI Cup on three occasions with Dundalk and he said he would always have special memories of his time at the club, irrespective of the outcome on Friday night.

“Dundalk FC has a special place in my heart,” he said. “They were very good to me, and my family, when I was here and I got a great ovation from the supporters before the game. It was great to be back.”

Current Bray Wanderers manager Ian Ryan, in action for Dundalk during the FAI Cup Fourth Round Replay against the Seagulls at Oriel Park in 2008. Photo by Sportsfile

Dundalk did meet Bray Unknowns in the second round of the FAI Cup back in 1929, a game notable for the goalscoring exploits of Eddie Carroll, who helped himself to four goals – a club record – in a 6-2 win, but this will be the third time that the Lilywhites have met Bray Wanderers in the competition.

Goals from John Cleary and Paul Newe secured Turlough O’Connor’s men a second-round 2-0 win at Oriel Park on their way to lifting the trophy in 1988.

The last meeting between the sides took place 15 years ago when the Seagulls won a replay at Oriel Park, 3-1, after a scoreless draw at The Carlisle Grounds.

Current Bray Wanderers manager Ian Ryan lined out for Dundalk in both of those games in 2008 and was also in the Wexford FC dugout last season when they pushed the Lilywhites in the same round with the 12-time cup winners eventually running out 3-2 winners after extra time.

“It’s a free hit for us,” Ryan told the Wicklow People. “Dundalk will have the heat on them and be expected to win and the reality is that they should win.

“But we’ll go with a plan and as we’ve seen; when we’re up against it, and we have a good crowd behind us, we come out fighting. We’ll give a good account of ourselves and we believe we can go and do something.

“I played Dundalk with Wexford in this round last year and it went to extra time so it’s not impossible. We’ll do our homework and be ready to go.”

Friday’s game will be streamed live on LOITV. A Match Pass costs just €5. Tickets are available online.