Lossiemouth first entered the Scottish Cup in 1954-55 when the Qualifying Cup was scrapped in favour of letting non-league teams enter straight into the First Round. Our first venture into the Scottish Cup was also one of our best as we managed to reach the Third Round, although Lossie didn't face SFL opposition and got knocked out by Highland League side Forres Mechanics, after a replay. 

1954-55
11/09/54: Lossiemouth 6-1 Murrayfield (Round 1) 
25/09/54: Lossiemouth 1-0 Gala Fairydean (Round 2) 
09/10/54: Lossiemouth 2-2 Forres Mechanics (Round 3) 
16/10/54: Forres Mechanics 5-3 Lossiemouth (Round 3 Replay) 

Next season it was still straight into the Scottish Cup again - and this season we went one better than before, reaching the Fourth Round. Our record from that season:

1955-56
10/09/55: Lossiemouth 7-0 Wick Academy (Round 1) 
24/09/55: Lossiemouth 3-1 Duns (Round 2) 
08/10/55: Lossiemouth 1-0 Selkirk (Round 3) 
22/10/55: Berwick Rangers 5-1 Lossiemouth (Round 4) 

The following season 1956-57 was the third and final season of automatic entry to the Scottish Cup before the Qualifying Cup was reinstated, but this time it wasn't a great one for us and we were bundled out at the first time of asking by Buckie of all teams.

1956-57
08/09/56: Buckie Thistle 4-0 Lossiemouth (Round 1)

With the Qualifying Cup reinstated, it wasn't actually that long before we tasted Scottish Cup football again and we qualified via the Qualifying Cup for the first time in 1957-58 where we faced now-defunct Glasgow outfit Third Lanark in probably the biggest game in our history. It wasn't to have a happy ending as Lossie were given a bit of a doing and sent home North again.

1957-58
15/02/58: Third Lanark 6-1 Lossiemouth (Round 2)

Then came the "big drought" and we didn't qualify for the Scottish Cup again until 1973-74 and, horror of horrors, we were drawn against fellow HFL side Fraserburgh, whom we went out to after a replay.

1973-74
15/12/73: Lossiemouth 3-3 Fraserburgh (Round 1)
17/12/73: Fraserburgh 6-0 Lossiemouth (Round 1 Replay)

Then it was another great drought and we didn't qualify for the Scottish Cup again until 1995-96, which is probably the first venture into the Scottish Cup remembered by the younger members of the support. Lossie were drawn away to Forfar where we put up a brave fight but were knocked out by 3 goals to one, with Gary Clark scoring late on to give the travelling support something to cheer on a bitterly cold day.

Programme cover from Lossies trip to Forfar in 1996 (click image to enlarge)

1995-96
06/01/96: Forfar Athletic 3-1 Lossiemouth (Round 2) 

Two years later, Lossie went into the hat again, with qualification made even sweeter due to it coming at the expense of Elgin City. With a replay at Borough Briggs looming large, a last minute goal by Dave Caldwell for ten man Lossie side ensured we went through and Elgin went out. This time we were rewarded with a home tie against Second Division Dumbarton - but the dream was short-lived as we fell to the SFL outfit one-nil despite playing them off the park for the whole game. This was probably the closest we had come to Scottish Cup glory. 

Local loon Stuart Simpson with the cup in 1997 (click image to enlarge)

Programme cover from Lossies last appearance in the Scottish Cup (click image to enlarge)

1997-98
03/01/98: Lossiemouth 0-1 Dumbarton (Round 2)

Another long wait was endured before Lossie once again qualified for the Tennents Scottish Cup, this time at the expense of Rothes. The draw produced a home tie against Spartans, one of the stronger East Of Scotland League sides, and with Lossie showing little in the way of form going into the game, the end result was no real shock. Craig Morrison had a goal disallowed early on, before Spartans went goal crazy, with Keith McLeod grabbing a hat-trick. If you are going to lose in the cup, you might as well do it in style.

2005-06
10/12/05: Lossiemouth 0-5 Spartans (Round 2)

The all-new Scottish Cup format saw Lossiemouth once again paired with East of Scotland opposition, this time in the shape of Whitehill Welfare. Familiar to the north from Cup games against Elgin City and Fraserburgh in recent years, the southerners proved to have a little too much for Lossie as they powered to a 3-1 win in an entertaining affair. Mark Wood scored for Lossie, Darren McConnachie saved a penalty to keep the hosts in the game, and David Blackhall had a late goal controversially ruled out for offside, but the visitors had done enough.

2007-08
29/09/07: Lossiemouth 1-3 Whitehill Welfare (Round 1)

In the second year of the new format Scottish Cup, Lossie were given a long haul away trip to Dalbeattie Star. Lossie went into half time leading thanks to a stunning Joe Lasley goal, but went down to ten men early in the second half when Kevin Stuart was sent off. Despite brave resistance from the visitors, the extra man advantage finally told and Dalbeattie ran away with the game late on, scoring twice in injury time.

This year Lossie host another South of Scotland side, Newton Stewart, and are looking to bring to an end a losing streak of almost 54 years in the Scottish Cup.

2008-09
26/09/09: Lossiemouth ?-? Newton Stewart (Round 1)