Il Lombardia wasn’t originally conceived as the grand autumn finale of the cycling season — it began as a localized grudge match cooked up in a Milan newspaper office.

In November 1905, Tullo Morgagni, an ambitious sports journalist for the Milanese newspaper Il Secolo, wanted to capitalize on a bitter rivalry between two star Italian cyclists: Giovanni Gerbi (known as Diavolo Rossdo for his fierce riding style and red jersey) and Giovanni Cuniolo (known a Manina (Little Hand), because he used to throw punches in the sporints!).

Gerbi had just won a local point-to-point race, but Cuniolo claimed he only lost due to mechanical trouble.

Recognizing a golden marketing opportunity, Morgagni organized a grand 230-kilometer race surrounding Milan to settle the score once and for all. He called it Milano–Milano.

On November 12, 1905, 54 riders set off from Milan into the cool autumn fog. Gerbi proved his dominance, launching a ruthless long-range attack to win the inaugural edition by over a stupendous 40 minutes in front of thousands of cheering spectators.

The race was an instant hit.

Seeing its massive success, the rival newspaper La Gazzetta dello Sport took over the event in 1907, rebranding it as Giro di Lombardia (later shortened to Il Lombardia). They shifted the route toward the dramatic, grueling climbs around Lake Como to test the riders’ endurance at the tail end of the season—giving birth to the Race of the Falling Leaves.

La Classica delle Foglie Mortes‘ autumn setting, brutal climbs and treacherous descents have produced some of the most dramatic stories in cycling history.

Fausto Coppi’s Dominance (1946–1949, 1954)

Fausto Coppi, Il Campionissimo, turned Il Lombardia into his personal playground, winning it a record five times. His most legendary victory came in 1946: Coppi launched a solo attack on the climb of the Madonna del Ghisallo with 80 kilometers left to race, crossing the finish line in Milan more than 11 minutes ahead of his closest rival, Luigi Casola. He went on to win four consecutive editions from 1946 to 1949.

Eddy Merckx Stripped of Victory (1973)

In 1973, Eddy Merckx looked to have captured his third Lombardia crown after out-sprinting Felice Gimondi in a reduced group finish in Verona. However, post-race anti-doping controls revealed traces of the banned stimulant Mucorex (used to treat chest infections, its compounds relax the smooth muscles surrounding the bronchioles, widening the lungs’ airways) in Merckx’s urine. Merckx was disqualified and the victory was awarded to Gimondi.

The Tragedy and Triumph of the Madonna del Ghisallo

The climb to the chapel of the Madonna del Ghisallo—the patron saint of cyclists—is the spiritual heart of the race. Inside the chapel burns an eternal flame for fallen cyclists.

• In 1992, Italian rider Fabiano Fontanelli suffered a horrific crash on the descent of the Ghisallo, breaking several vertebrae.
• In 2006, Paolo Bettini won the race just 12 days after his brother Sauro died in a car accident. Tears streaming down his face, Bettini pointed to the sky as he crossed the line wearing the World Champion rainbow jersey.

Nibali’s Daredevil Descent down the Civiglio (2015)

Vincenzo Nibali (The Shark of Messina – why do Italians get the best nicknames?) secured his first Monument victory in 2015 with a masterclass in bike handling. On the steep Civiglio, Nibali dropped his breakaways not on the uphill but by plummeting down the treacherous, damp corners at breakneck speed. He opened up a gap on the descent that no one could close, cementing his status as one of the greatest descenders of his generation.

Remco Evenepoel’s Miraculous Survival (2020)

During the 2020 edition, young Belgian phenom Remco Evenepoel was chasing down the lead group on the high-speed descent of the Sormano. On a sharp left-hand bend near a bridge, he clipped a low stone wall and flipped over the barrier, plunging 9 meters (30 feet) into a ravine. He suffered a fractured pelvis and a right lung contusion. Miraculously, he survived without head injuries, rehabilitated, and well, look at him now!

Tadej Time (2021–2025)

In recent history, Tadej Pogačar has mastered the race and his opponents. Starting with his victory in 2021, Pogačar reeled off consecutive wins year after year, matching and challenging Fausto Coppi’s historic records with explosive long-range attacks on the Civiglio and Passo di Ganda.

Some race for one race!