Lack of cash meant few signings and a reliance on the squad that had gained promotion. Stuart Golabek came from Ross County and Kevin Byers from Raith Rovers. Mid season Davide Xausa and Dennis Wyness joined but Paul Cherry and Iain MacArthur retired through injury. Scott McLean left for Queen of the South and Barry Robson went on loan to Forfar. A new kit sponsor came on the scene - Errea of Italy.
After a series of pre-season friendlies the first competitive match took place on 31 July - away at Stenhousemuir in the first round of the CIS Insurance Cup. It proved to be a stroll in the sun and Caley Thistle won 3-1. The start of the League campaign the following week was another matter - a 4-0 defeat away to Dunfermline demonstrated how hard things were to be in Division One. In the CIS Cup St Mirren were beaten but there was a narrow 1-0 defeat in the third round against Motherwell. The resurrected Bells Challenge Cup provided a good run to the final before losing to Alloa 5-4 on penalties after a 4-4 draw. It was a thrilling match with Caley Thistle coming back three times in normal play and once in extra time. The league was a real battle and the first four matches were lost. It was 4th September before a precious point was gained against Morton then the first win came the following week - 1-0 against Clydebank. The North Cup was lifted on 12th September with the 3-0 defeat of Lossiemouth and the Inverness Cup was won by beating Forres 6-0 on 24th November. League form improved and by Xmas Caley Thistle lay 6th equal with Airdrie - despite a 5-1 drubbing by Morton on 12 November.
The last game of 1999 was against Clydebank at home. Barry Wilson created Scottish football history when he scored the 4th goal - it was the last league or cup goal of the old millennium - helped by the 330 start. Amazingly he scored the first of the new millennium at Livingston on 3 January - a 1pm kick off because Livingston temporarily had no lights. Restructuring of the Board early in January saw David Sutherland take over as Chairman with Ken Thomson as Vice-Chairman. 8th January saw a 6-2 victory against Morton then the Scottish Cup draw the next day produced a plum away tie against Celtic.
The game drew great interest and 4000 fans made their way to Glasgow on buses, cars and a special train. After a night of gales part of the Parkhead stand became dangerous and the game was called off 45 minutes before kick-off. The disappointed supporters made their way home and the match was re-scheduled for 8 February - a Tuesday evening. They could not believe what was to follow as their team beat Celtic 3-1. This was dubbed the greatest Scottish football shock for over 30 years amd it spawned the classic headline "Super Caley Go Ballistic Celtic Are Atrocious" in The Sun. The resultant publicity was overwhelming and began to overshadow all other matters. Inverness was the centre of attention for a long time. The 5th round tie on the 20 February was at home against Aberdeen - live on SKY TV. After an exciting game it was 1-1 and a replay at Pittodrie. This took place on 29th February and 4000 fans travelled east in hope. The team put up a good show but narrowly lost 1-0. Only a wonderful Jim Leighton save from a Paul Sheerin volley in the dying minutes stopped a draw.
Richard Hastings and Davide Xausa both played in the replay after being with the Canadian international team at Gold Cup 2000 in California. Richard scored the winning quarter final "Golden Goal" against Mexico and he played in the final when Canada beat Colombia 1-0. Richard was also voted "Rookie of the Tournament". Davide played in the earlier games but missed the final due to a shoulder injury. Assistant manager Alec Caldwell left on February 24th to take the Manager's job at Elgin City - bound for the Third Division next season. Duncan Shearer moved into the vacant slot from First Team Coach. February was quite a month.
With the cup run over the new Board faced up to the economic realities of a near £2m overdraft and stringent financial controls were applied throughout the Club. On March 7 it was announced that there would be a £1m share rights issue. The terms were opposed by major shareholders but eventually agreement was reached and financial matters were set to dominate the close season. On the field the season was effectively over with 6th place in the League secure. It was just as well because a series of injuries decimated the team and gave chances to the Skillseekers. A 5-1 home defeat against lowly Airdrie on 15th April was a major embarassment but the season finished on a high note with a 5-0 home win against newly-crowned champions St Mirren.