He also played a great role in Grand Tours: he won Vuelta a España in 1998 and was second in 1995, made it twice to the final podium at Giro d'Italia (third in 1996 and second in 2001), and placed three times in the top-ten at Tour de France, with the fourth place in 1997 as his personal best. In total he won six stages in the Vuelta and one in the Tour, all of them time trials.
Olano was also double Spanish Champion in both road (1994) and time trial (1994 and 1998), olympic silver medalist in time trial in Atlanta 1996 and winner of several shorter stage races, like Tour of Romandie in 1996 and Criterium International and Tirreno-Adriatico in 2000.
Olano started racing 11 years old at the Oria Cycling school, and already at junior level he won several races. Later, Olano went to track racing. He became Spanish Champion in pursuit (together with Etxegoyen, Pérez and Juárez), in the 1 km with standing start and in sprint. In road racing, he started as an amateur for Kaiku and AVSA. He was specialized in sprinting.
In 1992, Olano started his professional career at CHCS. This team shortly after disbanded, and he moved to Lotus. With Lotus, Olano won his first professional race, the Gran Premio de Villafranca de Ordizia in Gipuzkoa.
In 1993, Olano switched to CLAS Cajastur, which was later merged with Mapei. Here, he started to win important races, such as the Vuelta a Asturias and the Spanish National Road Race Championships, both in road race and time trial.
In 1995, Olano won three stages in the Vuelta a España, finishing second in overall classification to Laurent Jalabert. Later in the year Olano was a vital part of a hugely successful Spanish team at the World Cycling Championship in Colombia. In the time trial, Olano took silver, finishing second to Miguel Indurain. In the Road race, the top two positions was reversed, with Olano taking the Championship and Indurain silver. The route for the road race was one of the hardest courses ever for a World Championship, and Olano showed his stamina by riding the last kilometer solo with a flat tyre.
Olano established his abilities in stage races in 1996; he won the Tour de Romandie, finished third in the Giro d'Italia (leading the race at the second to last day), and finished ninth in the Tour de France. He also won the silver medal in the time trial at the 1996 Olympic Games, losing out to Miguel Indurain by a margin of only 12 seconds.
Olano finished fourth in the 1997 Tour de France, taking 1 stage win - a long time trial in Disneyland, ahead of the eventual Tour winner Jan Ullrich.
In 1998, Olano won his only grand tour, the Vuelta a España, fighting off furious challenges from mountain specialistsFernando Escartin and Roberto Heras as well as fellow all-rounders Laurent Jalabert and Alex Zülle, all at the height of their careers. Despite the victory, Olano was reportedly not happy with the support from the Banesto team and management. Banestos own mountain specialist José Maria Jimenez took 4 stage wins, on several occasions leaving Olano alone on the climbs, and even taking the Yellow Jersey from his team captain. Olano won back the jersey on the second time trial, but the events and subsequent media speculation soured his relationship with Banesto, and he decided for a switch to the ONCE team for the following season.
Olano finished 1998 in style, winning the World Championship Time Trial i Valkenburg, ahead of compatriot Melcior Mauri. Olano is the only male rider of the modern era to win the world Championship in both the Road race (1995) and the time trial (1998).
In 1999, Olano was back to defend the Vuelta title. In the prologue, severe rains put the late starters (including most of the GC contenders) at a big disadvantage, but Olano nevertheless managed to take 2nd place. In the stage 7 time trial, Olano won with a clear margin to main challenger Jan Ullrich, taking the top spot on the GC and the Yellow Jersey. Olano defended his lead through several mountain stages, but a crash on the stage to Alto de Angliru cost him a broken rib, and he was eventually forced to abandon the race.
In 2000, Olano made a shift in focusing on shorter stage races, and won Tirreno-Adriatico and Criterium International, among others. He would make his last mark at the grand Tours with a 2nd place in the 2001 Giro d'Italia. He retired from racing in 2002.
On account of results early in his career, a Basque background and some physical similarities, Olano was seen by many supporters as the successor to five-times Tour de France winner Miguel Indurain. The comparison would haunt Olano for all of his career, as he went on to have a career that was very successful by almost any other standard. Olano was one of the very best time trialists of his generation, and a rider with enormous stamina. However, he was a reluctant climber, and a tendency to lose valuable time to the specialists on the steepest and highest climbs, would keep his number of Grand Tour Wins to 1.
Olano is one of the people responsible for designing stages for the Vuelta a España. He was fired from this position after a report from the French senate revealed that he had delivered a suspicious sample during the 1998 Tour de France, indicating use of EPO.
In November 2006 Olano ran the San Sebastian marathon in a time of 2:39:19. In October 2015, he took over as new national coach for Gabon, with the task of building the national team "from scratch"