Since gaining membership to the S.F.A. in season 1978-79 Annan have qualified for the Scottish Cup on seven occasions. Entry to the Scottish Cup is via the Qualifying Cup South where the four semi finalists qualify for the Scottish Cup proper.

Annan first encounter in the Cup saw them paired with Stranraer at Galabank on 15th. December 1979. A record crowd of 1250 were attracted to the match. In an enthralling match Annan were defeated 3-1 with Annans James “Bishop” Anderson having the honor of scoring Annans first ever Scottish Cup goal. The Annan team that day was Dick Kirkwood, Jim Beattie, Ronnie Kirk, Stuart Rome, Jimmy Fox, John Carmichael, Alan Irving, John Anderson, James Anderson, Willie Smith, Eddie McGauchie. Subs Colin Anderson and Anthony Sibbring.

Annans second encounter in the Scottish Cup gave the team an away tie at Somerset Park against Ayr United in the first round on the 6th. December 1986. Again Annan went down 3-1 but the performance merited the Annan team a standing ovation from the large traveling support who made the journey to Ayr. Annans goal on that occasion was scored by Colin Williamson which at that time brought the teams level mid way through the second half. Ayr on that occasion were managed by the ex Scotland manager Ally McLeod. The Annan team on that occasion was David Clark, Stuart Dalgleish, Colin Anderson, Lawrence Coulthard, Zoran Zutic,Tommy Proudfoot, John Sneddon, John Carmichael, John Wilson, Colin Williamson, David Learmont. Subs George Clark and Terrence Hanlon.

The clubs third Scottish Cup outing against Queens Park in the Second Round on the 7th. January 1989 proved to be the most disappointing to date with the visitors recording an easy 5-1 victory in front of another large crowd exceeding one thousand. Annans goal on that occasion came from Darrell Elliott’s spot kick after Tommy Proudfoot’s shot had been handled on the goal line. One of the interested spectators that day was former S.F.A. Secretary Ernie Walker. The Annan team that day was Chris Walker, Stuart Dalgleish, Colin Anderson, Stuart Rome, David White, Alan Findlay, Gordon Dick,Darrell Elliott, Tommy Proudfoot, Jeff Rayson, David Learmont. Subs Keith Middlemiss and George Clark. The Annan manager for the first three Scottish encounters was Sammy Wallace.

Annans fourth encounter and one of the most successful to date saw the side achieve a creditable 3-3 draw at Shielfield Park Berwick on 6th. January 1996. It was a memorable match which saw Annan coming from behind on three occasions to earn a replay at Galbank the following week. The Annan goals on that occasion were scored by Graeme Muir and a double from Philip Docherty which earned the “Doc” the Tennants man of the match award. The replay attracted a record 1650 spectators to Galabank but the home team were edged out 2-1 with substitute Paul Sibbring scoring Annans lone goal. The Annan team for both matches was drawn from the following players, Andrew Burnett, Grant Smith, Kevin Hetherington, Keith Middlemiss, Stan Leslie,Steven Leslie,Darrell Elliott, William Sim, Toby Patterson, Graham Muir, Phillip Docherty, Paul McGinlay, Paul Sibbring and George Hodgson.
The Annan manager on that occassion was Derek Frye.

Annans fifth venture in the Scottish Cup threw them into the Cup with a second round tie at Galabank against fellow East of Scotland side Vale of Leithen at Galabank on 3rd January 1998. Annan created club history by winning the match 3-1and progressing to the third round for the first time in front of nearly 1400 fans. Despite going down to a 5th minute John Hood goal , Annan staged a second half fight playing against a gale force wind , top goalscorer Normon Montgomery made ammends for missing a 56th minute penalty by heading home a Steven Hewitt cross a minute later. An own goal from David Gillie in the 76th minute and a 78th minute goal from Montgomerry sealed the match 3-1 in Annans favour. Annan team (4-2-4) Robert McColm, Keith Middlemiss, Jimmy Brown. Mark Sutherland, Kevin Proudfoot, Mark Nichol, Darrel Elliott, Gary Cochrane, Steven Hewitt, Normon Montgomery, Euan Bryson. Subs Alan Smith, Callum Graham,Michael Downie. In the third round Annan faced a long journey to face Second Division Inverness Caledonian Thistle at the new Caledonian Stadium on January 24th. 1998. It however turned out to be a fruitless journey for Annan who went down 8-1 to a good Calley side. Normon Montgomerry gave Annan an 8th. minute lead but the home side stormed to a 4-1 interval lead and added another 4 in the second half. Annan team Robert McColm, Keith Middlemiss,Mark Sutherland, Jimmy Brown,Stanley Leslie,Kevin Proudfoot, Darrel Elliott,Gary Cochrane,Alan Smith, Norman Montgomerry,Ewan Brydson, Subs Andrew Pratt, Michael Downie,Steven Hewitt. Annans manager for the campaign was Kevin Hetherington.

Annan celebrated the millenium with their sixth encounter in the Scottish Cup with a second round tie at Glebe Park Brechin on 8th January 2000. Annan earned their place in the Scottish Cup thanks to Qualifying Cup victories over Tarff Rovers ( 2-0 ) , Saint Cuthbert Wanderers ( 5-0 ) and Coldstream ( 3-1) the latter victory thanks to a second half hat trick by Marcus Thomson. In the semi final of the Qualifying Cup that season Annan went down 2-1 at Castle Douglas to Threave Rovers with ex Annan player Andrew Cook scoring the last minute winner after Annan had Elliott sent off in the 35th minute.

The match at Brechin proved to be another exciting match watched by a crowd of 436 the majority of which were Annan fans who made the long journey north. Brechin led 2-0 at half time thanks to a 27th minute Lee Bailey strike and a 41st minute Greig Smith shot. In an astonishing second half performance Annans Ryan McGuffie hit a glorious 51st minute goal and in the final minute substitute Alistair Sloan sent the Annan fans into dreamland with a precious equaliser. The Annan team on that occassion was Graham Potter, James Hannay, Paul Laurie, Kevin Proudfoot, Stan Leslie, Ryan McGuffie, David Irons, Mark Nicol, Phillip Docherty and Colin McMennamin, Subs Marcus Thomson, Alistair Sloan , Mark Little.

In the subsequent replay Manager David Irons stood by the same starting eleven but replacing Mark Little on the bench with Darrell Elliott who was suspended for the first match. It was another cracking cup tie which needed extra time to separate the teams who were deadlocked 2-2 after normal time. Phillip Docherty put Annan in front in the 26th minute but right on half time Jimmy Nairn equalised, the same Brechin player put his team 2-1 up in the 49th minute but in another grandstand finish substitute Marcus Thomson grabbed a precious equaliser in the 87th minute. The match was heading for penalty kicks before Roddy Black scored a glorious winner 8 minutes from the end of extra time. Crowd 1239. Over the two matches the Annan team were more than a match for their league opponents.

Annan’s seventh foray into the Scottish Cup under manager Harry Cairney was achieved in 2006-7 when Annan were awarded a bye in the first round and in the second round Annan entertained Greenock Morton who were top of the second division in the tie of the round on the 9th December 2006 in front of 1206 spectators. Annan were defeated 3-0 with all the goals coming in the opening half. Stuart Grecian gave Morton an 8th minute lead to make it an uphill task for Annan and further goals from Peter Weatherston in the 30th minute and Jamie Stevenson in the 38th minute gave the visitors a comfortable half time lead. Annan gave a good account of themselves in the second half but could not break down a resolute Morton defence . The Annan team on that occasion was – Dougie Calder, Scot Wilby, Russel McGuffie, Martin Bell, Stuart Hill, Mike Jack, Steven Sloan, Chris Jardine ( Gary McMenamin 48min ), John Hore ( Graeme Bell 74 min ), Simon Tucker, Ian Grainger. Substitutes Not used Fraser Paterson, Craig Allen, Gareth McCulloch.

The Scottish Cup format changed in season 2007-8 with all SFA members clubs now competing in the competition, four junior clubs join the non-SPL/SFL clubs in Round 1, Round 2 includes the winners of the East of Scotland Premier League and the South of Scotland League with 1st and 2nd from the Highland Football League along with all 10 division three clubs.

Details of Annan's matches along with comprehensive match reports can be found under the 'Matches' section within this website.