Garrido. Caballero made his first appearance in the SPL against Motherwell in a 2–0 away victory on 29 July. One week later, he scored his first goal in a 3–0 home victory against Dunfermline Athletic on 5 August. On 12 August, Caballero scored in a 5–1 away defeat against Hibernian and also received his first red card. On 23 August, Caballero scored a double in a 3–0 home League cup victory against Montrose. Four days later, he scored again in a 1–1 home league match against Hearts on 27 August, the goal being his fifth goal in four consecutive matches. During October 2000, Dundee opted to sign Claudio Caniggia as a replacement for Caballero who had surgery to repair a damaged knee and underwent extensive rehabilitation at a Bologna clinic. Caballero scored his fourth league goal in a 2–0 away victory against Aberdeen on 7 April. On 4 May 2001, it was reported by BBC Sport that Caballero had signed a new deal which would keep him at the club for the following three seasons. The club had paid an undisclosed fee to Paraguay's Club Sol de América to make Caballero's loan deal permanent and that the sum was significant enough to top the club record of £300,000 paid for Javier Artero. He scored his last goals of the season, a double, against Celtic, in a 2–0 away victory on 13 May. Dundee were eventually eliminated by Heart of Midlothian at the fourth round stage of 2000–01 Scottish Cup. Dundee eventually finished in 6th position of the SPL table, with 47 points, and qualified for the first round of the 2001 UEFA Intertoto Cup. Caballero ended the season having scored 6 goals in 15 league appearances and 2 goals in 2 League Cup appearances. 2001–02 season Dundee faced FK Smederevo of Serbia and Montenegro in the UEFA Intertoto Cup, where they would draw 0–0 at home in the first-leg on 16 June. In the second-leg on 23 June, Caballero scored in the 5th minute of the first half as Caballero was eventually red carded during the match. Dundee went on to be defeated 5–2. Caballero's first appearance of the 2001–02 Scottish Premier League season came in a 2–1 home victory against Hibernian, where Caballero scored the winning goal on 62 minutes, on 4 August. He scored his second league goal in a 4–1 home defeat to Aberdeen on 29 September.