Long-range attacks, 'kamikaze' descents and Via Roma victories – 10 ways to win Milan-San Remo

Editor's note: Ahead of this weekend’s Milan-San Remo, we went into the Cyclingnews archives to pull out this fantastic feature by our former Head of Features Barry Ryan, who in 2015 examined the different ways in which the race has been won over the years.

The pre-race chatter ahead of the 2026 Milan-San Remo is revolving around the expected Mathieu van der Poel vs Tadej Pogačar climbing battle in the men's race, and Lorena Wiebes chances of defending her title in a sprint in the women's race.

Already across the two editions this weekend, we can see how this race can play out in many different ways: one race is expected to blow up on the Cipressa, whilst a sprinter is the favourite in the other.

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In the microcosm of this year and last year, it might be easy to think that the attacking finales we've seen recently are the only ways Milan-San Remo can go, but in truth, the longest Classic of all also boasts the longest list of ways to win and candidates for victory.

In the breathless, high-tension finale, timing and tactics count as much as strength, and whether you go on the Cipressa, wait for the Poggio, go wild on the descent or even pounce on the Via Roma, there are multiple points at which the race can be won. Below are some of the most memorable.

The following feature originally appeared in 2015.

Solo clear on the Turchino – Fausto Coppi, 1946

It’s not easy to pinpoint precisely when and where Fausto Coppi transfigured into the quasi-mystical figure he is recalled as today, but the Turchino pass at the 1946 Milan-San Remo seems as likely a place as any.

By that point, Milan-San Remo’s late March date had already established it as La Primavera, the race that heralded the end of winter and the coming of spring, and the Turchino was the landmark of this liminality. Before the climb, the riders rolled their way through the frigid air of the northern Italian plain for one hundred miles. After cresting the summit, they dropped towards the glistening Riviera and the promise of spring.

The 1946 edition of Milan-San Remo was also the first after World War II and the bitter civil war that had followed the collapse of fascism in Italy, and that background only added to the symbolism of the race and its passage over the Turchino. Coppi was part of a five-man group that broke clear early on, and once on the slopes of the Turchino, he seemed to climb into another realm. The Frenchman Lucien Teisseire was the last man to stay in contact but he was inexorably distanced and Coppi emerged alone from the tunnel before the summit.

Over the 145 kilometres that remained, Coppi would build up a lead of 14 minutes to win alone in San Remo and the newspaper reports the following day couldn’t help but position the exploit within the wider context of Italy’s recent – and ongoing – unrest. “Coppi’s feat would simply have given a new lustre to a splendid athletic event, had another factor not conferred an undeniable symbolic meaning upon it,” Bruno Roghi wrote in La Gazzetta dello Sport. “Because of Coppi’s exploit, we feel unrepentantly Italian, Italians once again.”

Follow orders to the letter – Raymond Poulidor, 1961

As a rider, Antonin Magne won two Tours de France and a world title in the 1930s, but it is his afterlife as a directeur sportif that tends to recur most frequently in French cycling folklore. Magne’s eccentricities added much colour to the careers of Louison Bobet and Raymond Poulidor – he always wore a black beret and white shirt, and insisted on addressing his riders with the formal vous – while he also had a laconic command of language.

As Jacques Anquetil prepared to catch and pass Poulidor in a time trial at the 1962 Tour, for instance, Magne is reputed to have pithily instructed his rider: “Pull over, Raymond, and admire the Caravelle [the precursor to the Concorde – ed.]”

At the previous year’s Milan-San Remo, Magne’s plain-speaking was crucial in keeping Poulidor in the 1961 race and setting him up for victory. When the Frenchman punctured with 125 kilometres remaining, he sat on the roadside and began undoing his shoes, only for the Mercier team car to screech to a halt alongside him. “Raymond, I am forbidding you from abandoning. You have no right to do so,” Magne barked.

After re-joining the peloton, Poulidor followed Magne’s next orders to attack with Ab Geldermans and teammate Jean-Claude Annaert at the foot of the Capo Berta and then go clear alone on the Poggio.

Magne’s influence didn’t stop there, as Peter Cossins explains in his book The Monuments. “Rather than drive up behind his leader, Magne slyly followed Geldermans and Annaert, giving the peloton closing in behind the impression the three leaders were still together,” Cossins writes. “The ruse was enough to make the difference. ‘Poupou’ held on to win by 60m despite being sent off course by a policeman on the final bend.”

For once the Eternal Second landed the big win, thanks in no small part to the larger-than-life Magne’s influence. Had radio earpieces been around back then, maybe Poulidor might even have shaken off that nickname on the Puy de Dome in 1964.

Infiltrate the early break – Marc Gomez, 1982

Responding to the recurring lament that the Milan-San Remo route had become too easy, organiser Vincenzo Torriani added the climb of the Cipressa to the finale in 1982, and the expectation was that the new ascent would prove decisive. Perhaps it did, albeit in a rather indirect way.

There was no undue concern in the peloton when an early break of 13 built up an advantage of ten minutes on the long haul across the Plain of Lombardy, but the response – when it finally did come – was ruinously disjointed.

The favourite Giuseppe Saronni had already pulled out on the Turchino, having failed to dress adequately for the cold and wet conditions, while Francesco Moser’s Famucine squad and a young Moreno Argentin’s Sammontana outfit squabbled over whose responsibility it was to chase. Perhaps there was concern, too, about the extra difficulty posed by the Cipressa in the finale. In any case, it was increasingly apparent that the spoils would fall to a surprise winner.

By the time they hit the Cipressa, the break was already dwindling and just two riders, the Frenchmen Marc Gomez and Alain Bondue, remained out in front after crossing the summit. The pair still had three minutes in hand by the Poggio, and in the end, it was the treacherous descent that separated them. Bondue’s wheels slipped not once, but twice, and although the bespectacled Gomez seemed to tackle the hairpin bends in instalments, he stayed clear to win by 10 seconds, as Argentin pipped Moser in the sprint for third.

The 26-year-old Gomez was a neo-professional with Wolber and a most unlikely winner – Il Corriere della Sera grumbled that it was the first win from an early break since 1927 – though he went on to prove his worth by winning the prologue at the Vuelta a España that April and the French title the following year.

The unfortunate Bondue, meanwhile, would suffer a similar fate two years later at his home race Paris-Roubaix, when he crashed out of the winning break as he strained to follow Sean Kelly on the pavé.

Get away before the Cipressa – Gianni Bugno, 1990

Strange things were beginning to happen in cycling by 1990, the same year that Gianni Bugno won the Giro d’Italia after leading the race from start to finish and dominating on all terrains.

He began that particular annus mirabilis with a career-altering victory at Milan-San Remo – at a record average speed of 45.8kph – that marked his passage from eternal promise to an apparent heir to Fausto Coppi.

Introverted, pensive and softly-spoken, Bugno’s guarded exchanges with the press earned him the moniker of Vedremo – “We’ll See” – from Italian journalist Gianni Mura, and that same reticence seemed to blight him on the bike. The quiet man from Monza had entered the professional ranks in 1986 with a glittering reputation, but proceeded to frustrate observers with his tendency to second and even third guess himself in the finale of major races and miss out on the biggest prizes.

Bugno’s instinct won out over reason in the 1990 Milan-San Remo, however.

Crosswinds along the Riviera had broken up the peloton earlier than normal, scattering it into three large echelons, and when Angelo Canzonieri took a flyer off the front after passing Imperia, Bugno – for once – didn’t think twice about tracking the move. Once on the Cipressa, Bugno pulled clear alone and had 15 seconds in hand on the chasers over the Poggio.

Although Rolf Gölz stalked Bugno all the way to San Remo, he held on to become the first home winner of La Primavera since Moser six years earlier, and his victory was to pre-empt a decade of classics dominance for Italy and its teams.

“Is the world changing, or at least Italy?” Gian Paolo Ormezzano wrote in La Stampa the following day, with perhaps inadvertent foresight.

Descend the Poggio "like a kamikaze pilot" – Sean Kelly, 1992

Milan-San Remo is the classic with the widest spread of genuine contenders, but in 1992 Moreno Argentin lined up as the overwhelming favourite for victory. One of the first riders to enjoy the full benefits of Dr. Michele Ferrari’s particular area of expertise, Argentin had raised eyebrows all spring, first by dominating the Settimana Siciliana and then by winning the last three stages of Tirreno-Adriatico with disarming facility.

Argentin launched four accelerations on the way up the Poggio before finally punching his way clear. and with his pursuers scattered across the hillside, he crested the summit clutching what looked to be a winning gap. The host broadcaster’s cameras focused on Argentin as he plunged down into San Remo, but an aerial shot towards the base of the descent suddenly showed that Sean Kelly, seemingly irretrievably distanced on the climb, was now closing in dramatically.

Kelly bridged across as Argentin entered the final kilometre, and shook off repeated entreaties to share the pace-setting in the streets of San Remo. He sensed Argentin’s panic.

Milan-San Remo was the race Argentin coveted above all others, while Kelly – already the winner in 1986 – was by now 35 and widely held to be in decline. A desperate Argentin opened his sprint early and Kelly – seemingly unencumbered by his bulbous white helmet – easily came around him for the win, the last man to claim La Primavera in toe clips and straps.

“If Milan-San Remo finished on top of the Poggio, I’d feel pretty certain of winning. I don’t know why, but I haven’t been descending well lately,” Argentin had said prophetically before the race.

“I realised Argentin was losing five metres on every bend,” Kelly said afterwards. “He was braking, but I was going down like a kamikaze pilot.”

We tapped up Sean Kelly for his thoughts and predictions before this year's race. His view? Isaac del Toro is the danger man.

Matej Mohorič famously won in a similar fashion in 2022, using a dropper seatpost to get extra tucked on the descent and fly to victory.

Motor away on the Poggio – Giorgio Furlan, 1994

By the mid-1990s, Milan-San Remo had begun to follow an unnerving template. The leaders would hit the base of the Poggio at breakneck speed and then the strongest man would simply motor away on the climb in a monstrous gear, often catching the slipstream of the photographers' motorbikes.

Not surprisingly, the record time for the Poggio dates to this period, even if it still a matter of internet debate as whether it belongs to 1995 winner Laurent Jalabert or his predecessor Giorgio Furlan.

For the record, Dr. Michele Ferrari clocked Furlan’s time at 5:45 (for a startling average speed of 38.5kph) and, well, he ought to know. Ferrari was the preparatore for Furlan and his Gewiss team during their remarkable 1994 season, when along with Milan-San Remo, they also claimed a clean sweep at Flèche Wallonne, Liège-Bastogne-Liège with Evgeni Berzin and the Tour of Lombardy thanks to Vladislav Bobrik. For good measure, Emanuele Bombini’s men also won the Giro d’Italia through Berzin and took second place at the Tour de France with Piotr Ugrumov.

A professional for over a decade, Furlan’s major victories were shoehorned into a remarkable two-year spell in the middle of his career, with the apogee arriving in the spring of 1994. Furlan arrived at La Primavera fresh from winning three stage wins and the overall at Tirreno-Adriatico, and it was clear from the foot of the Poggio that there could only be one winner.

“They’re going uphill and they can hardly get around the corner they’re going so quickly,” Phil Liggett says in his commentary as Berzin drills on the front for Gewiss on the Poggio. “It takes an awfully fit man to do this at this point in the race,” he adds later, as Furlan opens his winning gap and solos clear to win by 20 seconds.

A month later, Ferrari was – notionally at least – sacked by Gewiss following his most notorious public declaration on EPO use. It would take a little longer for the speeds on the Poggio to drop.

Rely on the kindness of strangers – Erik Zabel, 1998

Gabriele Colombo emerged from obscurity to land Milan-San Remo in 1996 and though he would never scale those heights again, the Varese native did at least make a point of popping up in the finale of La Primavera thereafter, almost like an Alfred Hitchcock cameo. The most infamous such appearance came in 1998 in the colours of Ballan.

The veteran Alberto Elli, then riding for Casino, appeared to have a winning advantage when he crested the summit of the Poggio alone in front, while the defending champion and pre-race favourite Zabel had no Telekom teammates for company in the chasing peloton.

On the plunge into San Remo, however, the fair-haired Colombo hit the front of the bunch, and his long turn eventually saw Elli swept up 600 metres from the finish. Zabel duly saw off Emmanuel Magnien in the sprint, but the Italian press at the finish line had eyes only for a polemica when they clocked Elli shouting “Venduto!” as he pushed his way through the bodies in search of Colombo.

“What sense is there in towing along someone like Zabel who’ll only beat everyone in the sprint? If someone does that, the reason is clear,” Elli told reporters. “If that’s not riding for Zabel, then tell me what it is.”

For his part, Colombo insisted that he hadn’t realised that Zabel was on his wheel – “I was just trying to go all the way to the finish” – but this particular colpo di scena clamoroso would keep the home press going for weeks.

Ironically, however, Elli would himself sign for Zabel’s Telekom team at the end of that season.

Pre-empt the sprint – Andrei Tchmil, 1999

The 1999 edition of Milan-San Remo was supposed to pit Michele Bartoli’s instincts as a puncheur against Erik Zabel’s qualities as a sprinter, with Marco Pantani as something of a wildcard.

Milan-San Remo was never a race suited to Pantani’s characteristics but after landing the Giro-Tour double the previous year, he was compelled to put on a show. And if his input could discommode Bartoli – with whom the Italian press had been trying to whip up a rivalry since the first week of the 1998 Giro – so much the better.

Pantani set the tifosi’s hearts aflutter when he bounded clear on the Cipressa, and Bartoli, riding for his new team Mapei in the colours of World Cup champion, felt honour-bound to respond. Their group swelled to eight riders ahead of the Poggio, but a distinct lack of collaboration meant that their endeavour was doomed from the outset. After the then-annual Gabriele Colombo dig over the Poggio, the race looked set to play out with the inevitable Zabel sprint win.

Inside the final kilometre, however, there was an unexpected ad lib.

Swinging onto the Via Roma, Andrei Tchmil attacked and suddenly found he had 20 metres in hand over the peloton. He had chosen his moment sagely. Zabel launched a long sprint in a desperate bid to get back on terms, but he had to settle for second place, as Tchmil broke up his winning sequence with a sniper’s move.

“I wasn’t worried by Pantani and Bartoli’s attack,” Tchmil shrugged afterwards. “I knew they wouldn’t work together.”

All in the timing – Óscar Freire, 2004

After claiming 15 stage wins in Grand Tours in 2003 and then dominating the flat days at the Giro della Provincia di Lucca and Tirreno-Adriatico, the onus was on Alessandro Petacchi to confirm his status as the world’s pre-eminent sprinter by landing victory on the Via Roma in 2004.

The strength of his Fassa Bortolo team only strengthened his billing as consensus favourite, and as the road flattened out after the descent of the Poggio, he was tucked in behind no fewer than five of his teammates. Victory seemed inevitable.

Filippo Pozzato, Marco Velo and Guido Trenti duly provided a pitch-perfect lead out for Petacchi but the man from La Spezia made the critical error of assuming that a sprint at the end of 300 kilometres of racing would be no different to any other. He opened his effort too soon and he faded in the final 100 metres, crossing the line in fourth.

“I didn’t remember that the road climbed slightly and maybe I opened my sprint a bit too early,” Petacchi conceded.

Petacchi, of course, wasn’t the only man to be caught out. Erik Zabel had been locked onto the Italian’s wheel in the closing kilometres and, not unreasonably, based his sprint around that of the pre-race favourite. His critical error was to assume that beating Petacchi would equate to winning his fifth Milan-San Remo.

Zabel even raised his arms in celebration – only for Óscar Freire to nip past him and steal victory on the line.

“I was sure I'd won because I'd gone past Petacchi, I just didn't see Freire coming up," a chastened Zabel said.

Not for the last time, Freire had pulled off a heist worthy of a George Clooney caper.

Make one effort, and make it count – Óscar Freire, 2010

Eddy Merckx’s record of seven wins will surely never be touched, but while Erik Zabel earned himself the title of Signor Sanremo after his four victories, the true modern master of La Classicissima was surely Óscar Freire.

His third and final victory in 2010 was perhaps the finest illustration of how the race so chimed with his skills as a rider.

All the way up the Poggio, his fellow fast man Alessandro Petacchi could be seen battling gamely to stay in fourth position, eager to track every move on the climb. As the elongated leading group approached the summit, Freire was ten places back, just behind Tom Boonen, and as the elastic stretched to breaking point on the way down, he seemed to disappear from view altogether. Other sprinters could be seen desperately scrambling to get back to the front. Thor Hushovd put in a mammoth turn to close a gap, for instance, and Daniele Bennati’s Liquigas team were prominent.

As the race eddied all around him, however, Freire made no attempt to beat against the current. His calm in a seeming emergency was rewarded – after a general regrouping as the road flattened out in San Remo, the Spaniard was tucked onto Bennati’s wheel in third place.

Freire won the sprint on the temporary Lungomare Italo Calvino finish by the proverbial street.

The modern trend for course design is to pitch races as strongest man contests – witness the alterations to the Ardennes Classics over the years and, more recently, the Tour of Flanders – but Milan-San Remo, that glorious anachronism open to any outcome, remains the quintessential thinking man’s race.

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