In the first round, the club was drawn to play the 5th K.R.V., one of the two strongest sides in the region, and who had beaten the Mids 10–1 in the competition two years earlier.

[5] The Volunteers protested, but, after a 4–4 draw in the re-played tie on neutral territory at Milldamhead (the ground of Vale o' Nith),[6] they failed to turn up for a replay, and the Mids were put through to the second round.

Reflecting the Lockerbie fans' hopes for success, there was greater support at the match for the visiting Volunteers; the "indifferently represented" Mids took a two-goal lead early on, but the 5th scored 5 goals before half-time, and ultimately won 11–3.

[14] The 5th also dealt a heavy defeat to the Mids in the final of the Charity Cup at the end of the season at Cresswell Park in Dumfries, this time 8–2, although by this time the Mids had recovered the previous season's players Ross, Laidlaw, Gardiner, and James Mitchell to their ranks; blame for the defeat was put on the "feeble resistance" offered by inexperienced goalkeeper M'Kinnon.

[15] The Mids met the 5th again in the second round of the 1890–91 Scottish Cup; Mid-Annandale had recorded its record victory[16] in the first round, hammering Rising Thistle of Lochmaben 16–1,[17] but the Volunteers again came out on top, the game ending after 75 minutes with the score at 9–1 after Mundell left the pitch in protest at the refereeing; W. Mitchell, Robert Steel, and Ross having already done so, thus leaving the Mids with 7 men.

[19] The club's tie at that stage with the original Aberdeen club in 1891–92 was scheduled to be played at Duckburn Park in Dunblane[20] but the referee postponed the tie because of a frozen pitch; the Mids, being "working fellows" and a "sturdy lot", offered to play regardless, which was declined by the "genteel" Aberdeen side of "clerks, teachers &c", and the sides nearly came to blows over the issue, much to the amusement of the locals.

[22] The second round proper, made up of 16 clubs, and the furthest the club would ever reach, saw Mid-Annandale drawn to play the Scottish League side Cowlairs away from home, and suffer an 11–2 defeat; the home side missed a penalty, but scored seven goals without reply in the second half, and one of the two Ross brothers was sent off with 10 minutes to go, his brother also leaving the pitch in sympathy.

Yet again the Mids saw players leaving the pitch as a protest against the refereeing, this time after Mitchell was sent off for "kicking an opponent while lying on the ground", joined by the two Rosses and Richardson.

When beating whipping boys Rising Thistle 14–0 at their Innerfield Park in the first round match, "the latter portion of the game was characterised by a display of roughness on the part of the visitors", with Mitchell being singled out for violence.

[35] The club's colours were light blue until 1887,[36] and yellow (originally described as orange[37]) and black striped shirts afterwards, with navy knickers.