2005 season

At Lampre, Bennati grew from a promising domestique into a top sprinter. This transition was not instantaneous: early in 2005, he finished sprints behind both his old leader Cipollini, and teammate Giosuè Bonomi. Nevertheless, he accumulated a number of good finishes: 5th in a stage of Tirreno–Adriatico and 28th at Milan–San Remo. His first important result was in Gent–Wevelgem, where he outsprinted Thor Hushovd and Fabian Cancellara for 3rd place, behind the breakaway of Nico Mattan and Juan Antonio Flecha. He tested positive for Betamethasone after the race, but was only handed a warning by the Italian Cycling Federation.^[5] A few weeks later, Bennati won the Giro di Toscana. He did not compete in the Giro d'Italia – where Lampre concentrated on the overall victory with Gilberto Simoni and Damiano Cunego – nor did he ride the Tour de France. In August, he won three stages and the points jersey in the Tour of Germany, and had good placings in important races such as the Grand Prix de Plouay (4th), the Coppa Placci (5th), and the Giro di Romagna (2nd). September brought two more stage victories in the Tour of Poland. Thanks to these results, he was chosen for the Italian national team that competed in the UCI Road World Championships in Madrid, but the team leader, Paolo Bettini, finished only 13th. At the season's close, Bennati was ranked 28th in the UCI Pro Tour standings, and had become a rider to watch.

2006 season

During the off-season, Bennati's team changed its secondary sponsor, becoming Lampre–Fondital, and signed another promising Italian sprinter, Danilo Napolitano, setting up a competition for the top sprinter's spot on the team. Bennati started the 2006 season with two second places in the Gran Premio della Costa Etruschi (behind Alessandro Petacchi, who had taken over Cipollini's mantle as the dominant Italian sprinter), and then took his first win of the season in February's Volta a la Communitat Valenciana, four seconds ahead of the peloton, led home by Napolitano. In March, Bennati was due to be the team's leader for the important races. He probably was not at his best form when he started the Tour of Flanders, and he had to drop out. He was then unable to start the Gent–Wevelgem race. Ten days later, however, a fully recovered Bennati won the final stage of the Giro del Trentino, won overall by teammate Cunego. The next week, he competed in the Tour de Romandie, where Robbie McEwen showed that Bennati was not quite at the top level.

The Lampre team for the Giro d'Italia was again built around the overall competition, and Bennati was not included. Instead, he participated in the Volta a Catalunya, winning the final stage ahead of Erik Zabel. In early June, he outsprinted his two breakaway companions to win the Memorial Marco Pantani. Although he could only manage 2nd and 3rd places in the Tour of Switzerland, he did wear the leader's jersey for one day and won the points jersey. July brought Bennati to his first Tour de France; he was among the top ten finishers in eight stages, including a 2nd place behind McEwen. He dropped out after a fall during the 16th stage; he was third in the points jersey competition at the time. Two months later, Bennati returned to the Tour of Poland, where he won two stages and wore the leader's jersey for two days.

The following weekend, he won two more races: the GP Citta di Misano-Adriatico and the Gran Premio Industria e Commercio di Prato, but was not chosen for the Italian UCI Road World Championships team, as selector Franco Ballerini opted to do without any sprinters. Although his result in the sprinters' classic, Paris–Tours, was disappointing (37th), Bennati ended his season with a victory at the Giro del Piemonte. This brought him to a total of 9 victories in 2006, but he dropped to 87th place in the Pro Tour standings – largely due to his absence from the spring classics due to illness.

2007 season

Bennati spent much of his off-season training in the Canary Islands (with Daniele Righi, Giuliano Figueras, Caudio Corioni, and Mauro Santambrogio) and began the 2007 racing season with two wins in February. In the Tour Méditerranéean he won one stage, with strong support from his teammate Alessandro Ballan, had two 2nd places – marginally beaten in one stage by Mirco Lorenzetto – and won the points jersey. After a fourth place at the Trofeo Laigueglia, Bennati outsprinted Alessandro Petacchi for three wins in the Volta a la Communidat Valenciana. Unlike previous years, Bennati did not compete in Tirreno–Adriatico, choosing to ride Paris–Nice instead, where he had some high finishes but no victories. Once again, he was stricken by illness just prior to Milan–San Remo, where he finished 26th, and the Grand Prix E3 was a disappointment for the same reason.

Bennati's form improved in the beginning of April, where he won one stage of the Dreidaagse De Panne. In the Tour of Flanders, he worked hard for Ballan, who won in a sprint ahead of Leif Hoste. Although he was one of the favorites for the mid-week classic Gent–Wevelgem, Bennati had to withdraw because of a fever and intestinal difficulties. He started Paris–Roubaix but did not make it to the finish. His troubles continued into May; Bennati had to drop out of the Volta a Catalunya, though he did manage a third place in one stage. In the Tour of Switzerland he recovered his health and won the points jersey; although he had no stage victories, he had a second place in the prologue, behind Fabian Cancellara, and second places in two other stages as well, behind Erik Zabel and Robbie McEwen respectively. A few days later, Bennati took 6th place in the Italian National Road Race Championships.

In July, Bennati rode in the Tour de France for the second time; he now had enough stature that his goals of winning a stage and competing for the points jersey were considered reasonable. As his team had no rider for the overall standings, he could count on help from his teammates Ballan, Napolitano, and Corioni. However, he fell in the last kilometer of the second stage and was not able to unleash his sprint until he had recovered somewhat from his injuries. In the fifth stage, he finished 3rd, behind Filippo Pozzato and Óscar Freire. There followed a 6th place, a 4th place, some unsuccessful breakaways, and then, after the last mountain stages, Bennati won twice, including the prestigious final stage on the Champs-Elysees. On the strength of his successes, he was named the leader of the Lampre team for the Vattenfall Cyclassics race, but watched as his teammate Ballan took off from the peloton and held on to win.

In September, Bennati raced in his second Grand Tour of the season, the 2007 Vuelta a España. He won the first stage ahead of Freire and Petacchi]], and wore the leader's jersey for a day, losing it after a fall two kilometers from the finish of the second stage. After two second places, he came into his own during the final week, just as he had in the Tour de France: Bennati won the 17th stage and then the final stage in Madrid, taking the leadership in the contest for the points jersey on the final day of the race. This victory, his tenth of 2007, marked the end of Bennati's season. Although he had been scheduled to compete in the Monte Paschi Eroica and Paris–Tours, he was found to have a broken wrist that ruled out any more racing.

During the final week of the Vuelta a España, Bennati had signed a two-year contract with a new team: Liquigas. Claudio Corioni and Enrico Franzoi, valuable teammates who formed an important part of his leadout train, also signed for Liquigas.

2008 season

Bennati at the 2008 Philadelphia International Championship.

The move to Liquigas brought up some potential frictions: they now had two stars, Bennati and Filippo Pozzato, whose primary targets for the year would be similar. Any conflict in their spring racing goals disappeared, however, with Bennati's knee injury – a slight patellar chondropathy in the left knee, associated with inflammation of the lateral ligament – keeping him out of action until the end of April. He did not finish his first race back (the Giro d'Oro, but in his next race, the Giro del Trentino, he took 17th in the opening time trial but did not figure in any of the stage finishes. The Tour de Romandie opened with a very short prologue, where Bennati took second behind Mark Cavendish. He also took second behind Robbie McEwen in the first sprint finish, showing that he was coming back into form. This was confirmed with a victory in the final stage, giving him first place in the points classification.

The 2008 Giro d'Italia was a success for Bennati, and was marked by a series of battles with Cavendish. Bennati won the third stage, into Milazzo; the following day, Cavendish won the stage to Lungomare, his first Grand Tour win. The next sprinters' stage was the ninth; Bennati won, by a whisker, over Paolo Bettini, who was racing his final Giro d'Italia. Bennati also won the 12th stage, with a narrow margin over Cavendish; the order was reversed the following day. His three stage victories in a Giro with few stages suitable for sprinters also gave Bennati the points jersey. However, Bennati paid a price for the points jersey: the long pull in cold weather over the Mortirolo Pass caused an inflammation of Bennati's left Achilles tendon, the same leg as the knee injury.

He did not return to competition until August, at the Eneco Tour. There he was second to Tom Boonen in the second stage before winning the third stage and taking the leader's jersey for a day. He was dropped in the fourth stage, finishing in 88th place 22 seconds behind Boonen and losing the lead in the GC to André Greipel. Bennati then dropped out of the Eneco Tour and proceeded to the Vuelta a España in good form – where Pozzato was also a team leader. The Liquigas team won the first stage, a team time trial, with Pozzato crossing the line first and donning the leader's jersey. Bennati served as a domestique for Pozzato during the second stage, but when Pozzato did not retain the leader's jersey he was able to ride for himself. He was 2nd to Boonen the following day, and then won the fourth stage, ahead of Boonen but dropped out after the 9th stage. Bennati was not named to the Italian team for the UCI Road World Championships, and his bad luck in Paris–Tours, the sprinters’ classic, continued; he finished 8th in a race won by Philippe Gilbert. However, Bennati won his final race of the year, the Giro del Piemonte; it was his second victory in this race, which he also won in 2006.