The match was Alloa Athletic's first national cup final in its 121-year history[2] whilst it was Inverness Caledonian Thistle's first since the club was founded five years beforehand in 1994.

[4] The competition is a knock-out tournament and in 1999 was contested by the 30 teams that played in the First, Second and Third Divisions of the Scottish Football League.

The scoreline was 0–0 most of the game until Paul Sheerin scored a late winner for Inverness in the 88th minute to win the match 1–0 for the club.

[11] The second round also saw Alloa drawn away from home; facing First Division club Airdrieonians at Excelsior Stadium.

With Airdrie the favourites to win the match, Alloa took a shock 2–0 lead with goals from Mark Nelson and Gregor McKechnie.

Airdrie scored a consolation goal in the last minute from Forbes Johnston to make it 2–1, but Alloa held on to win and progressed to the quarter-finals.

Alloa replied with a goal from Scott Bannerman and then a penalty in the 80th minute from Willie Irvine to win 2–1 and reach the final.

[14] In order to reach the final, Alloa played all four matches in the preceding rounds away from home, keeping only one clean sheet and recording three successive 2–1 away wins.

[15] Alloa were in good form before the match, losing only three of their previous 22 games in all competitions since the start of the season in late July.

[16] At the time of the final, Alloa were equal on points at the top of the Second Division table but ranked third on goal difference.

[14] Alloa scored the first goal of the game in the 19th minute with a 12-yard shot from Gary Clark when Inverness failed to clear the ball from a corner kick.

[14] Referee Jim McCluskey awarded Inverness their second penalty kick of the game ten minutes later when Alloa defender David Beaton handled the ball in the box and Sheerin again equalised the scoreline at 3–3.

Between the 65th and 67th minute, Alloa made the first substitutions of the game: Mark Wilson and Gary Clark were replaced by Gregor McKechnie and Max Christie respectively.

Alloa managed to keep the score at 3–3 for the rest of the match until the full-time whistle to force the game into extra time.

[14][22] Match rules The trophy was presented to Alloa captain Craig Valentine after the game by Lord Macfarlane of Bearsden.