The Highland Amateur Cup is an annual football cup competition run by the Highland Executive branch of the Scottish Amateur Football Association. All teams affiliated to Highland Associations are eligible to enter the competition and therefore this competition covers one of the biggest geographiocal areas for any district amateur cup competition. Currently the affiliated associations to this competition are Caithness AFA, Sutherland AFA, North West Sutherland AFA, Ross-Shire AFA, Skye & Lochalsh AFA, Lewis & Harris AFA, Uist & Barra AFA and Orkney AFA. Shetland AFA clubs are eligible to take but due to travel distances have only entered the competition on two occasions.

The semi-finals are usually held at a neutral venue, with the final usually being held at the home of Ross County

Ross County F.C.

Ross County Football Club are a Scottish professional football team from the town of Dingwall, Ross and Cromarty. Founded in 1929 they currently compete in the Scottish Football League First Division and play their home matches at Victoria Park. Prior to the 1994–95 season they played in the...

, Victoria Park

Victoria Park, Dingwall

Victoria Park is a football stadium situated in the town of Dingwall, Ross-shire, Scotland. It is the home stadium of Ross County F.C. who currently play in the Scottish Football League First Division. It is the most northerly ground in the Scottish Football League.There are two stands; the West ...

.

Back

Back, Outer Hebrides

Back is a district and a village on the Isle of Lewis on the coast of Broadbay, in the Outer Hebrides, Scotland. The road through Back commences at a road junction in Newmarket, north of Stornoway. It is a little touristed part of the Hebrides despite having some of the best beaches in Lewis, but...

, who compete in the Lewis and Harris Football League

Lewis and Harris Football League

The Lewis and Harris Football League is the annual football league contested between clubs from the Isle of Lewis and the Isle of Harris in Scotland.Lewis contributes eight clubs to the league and Harris contributes one...

, won the cup in 2004.
Ness

Ness, Western Isles

Ness is the northernmost part of the Isle of Lewis, a community consisting of about 16 villages, including Lionel, Habost, Swainbost, Cross, North and South Dell, Cross Skigersta, Skigersta, Eoradale, Adabrock, Port of Ness, Knockaird, Fivepenny and Eoropie. It is the most north-westerly community...

, also of the Lewis and Harris Football League

Lewis and Harris Football League

The Lewis and Harris Football League is the annual football league contested between clubs from the Isle of Lewis and the Isle of Harris in Scotland.Lewis contributes eight clubs to the league and Harris contributes one...

, have won this competition on four occasions; 1984, 1991, 1992 and 1995. The 1984 competition was the first time a team from the Western Isles was allowed to enter and Ness' cup run ended with a 4–1 victory over Bishopmill Villa at Victoria Park, Dingwall. Lochs (2003 & 2005) and Point (1994) are the other Lewis and Harris Football League teams to have won this cup while Stornoway Athletic have been runners-up on two occasions (1990 and 2003). Contin reached the final in 1997 & 1999 winning the final in 1999. Pentland United have won the competition six times. Pentland United won the final in 2008 beating fellow Caithness

Caithness

Caithness is a registration county, lieutenancy area and historic local government area of Scotland. The name was used also for the earldom of Caithness and the Caithness constituency of the Parliament of the United Kingdom . Boundaries are not identical in all contexts, but the Caithness area is...

 team Castletown 3–0.

{| class="wikitable" border="1"
|-
! Highland Amateur Cup
! Past Winners
|-
| Year
| Club
|-
| 1978
| Blackmuir
|-
| 1979
| South Ronaldsay
|-
| 1980
| Thurso Pentland
|-
| 1981
| Thurso Pentland
|-
| 1982
| Halkirk
|-
| 1983
| Thurso Pentland
|-
| 1984
| Ness
|-
| 1985
| Halkirk
|-
| 1986
| Maryburgh
|-
| 1987
| Pentland United
|-
| 1988
| Kirkwall Thorfinn
|-
| 1989
| Dingwall Thistle
|-
| 1990
| Maryburgh
|-
| 1991
| Ness
|-
| 1992
| Ness
|-
| 1993
| Pentland United
|-
| 1994
| Point
|-
| 1995
| Ness
|-
| 1996
| Dingwall Thistle
|-
| 1997
| Kirkwall Rovers
|-
| 1998
| Pentland United
|-
| 1999
| Contin
|-
| 2000
| Pentland United
|-
| 2001
| Wick Thistle
|-
| 2002
| Pentland United
|-
| 2003
| Lochs
|-
| 2004
| Back
|-
| 2005
| Lochs
|-
| 2006
| Avoch
|-
| 2007
| Avoch
|-
| 2008
| Pentland United
|-
| 2009
| Kirkwall Thorfinn
|-
| 2010
| Pentland United
|-
| 2011
| Avoch
|-
Highland Amateur Cup Website
SAFA Website