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28.09.1999 @ 19:00 Caledonian Stadium, Inverness Attendance: 1025
Inverness CT
1 - 0
Livingston
Referee: M McCurry Challenge Cup / Semi Final-match

Goalscorers
None. None
Starting Lineup
Substitutes
Substitutions
None. None
Yellow cards
None. None
Red cards
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Match report
Caley Thistle booked their place in the Final of the Challenge Cup with a narrow victory over arch-rivals Livingston. It was not much of a game and it took a late Paul Sheerin goal to clinch victory. The winning goal came two minutes from time as extra time looked a certainty. Stuart Golabek ran infield from the left and found McLean. His shot came off the keeper and Sheerin was on hand to score from the rebound. Caley Thistle now play Alloa in their first ever senior cup final on November 21st.