Pogacar vs Van der Poel in Cycling’s Most Unpredictable Monument

The 2026 edition of Milan–San Remo, the first Monument of the season, promises another showdown between two of the sport’s biggest stars: Tadej Pogačar and Mathieu van der Poel.

Known as La Classicissima, Milan–San Remo is the longest race on the WorldTour calendar at nearly 290 km and one of the hardest races to win tactically. Despite its modest climbs, the combination of distance, positioning and explosive finales makes predicting the outcome extremely difficult.

In recent years, however, the race has increasingly become a two-man tactical battle between Pogacar and Van der Poel.

What Happened in Milan–San Remo 2026?

The 2025 race was one of the most dramatic editions in modern history.

• Pogacar attacked repeatedly on the Cipressa and Poggio.

• Only Van der Poel and Filippo Ganna could follow.

• The trio reached San Remo together.

• Van der Poel won the sprint ahead of Ganna and Pogacar.

2025 Podium

1. Mathieu van der Poel

2. Filippo Ganna

3. Tadej Pogacar

The decisive phase began on the Cipressa climb with about 25 km to go, where Pogacar’s team detonated the race. Only Van der Poel and Ganna survived the acceleration.

On the Poggio, Pogacar attacked multiple times but couldn’t shake Van der Poel. Ganna briefly dropped but rejoined on the descent before the final sprint.

The trio’s pace was extraordinary – the Cipressa climb record was broken by around 20 seconds.

Van der Poel launched his sprint about 300 metres from the finish to secure victory.

What 2025 Tells Us About 2026

The 2025 race confirmed several key trends that will shape Milan–San Remo 2026.

1. Pogacar Has Changed the Race

Historically, Milan–San Remo was decided on the Poggio climb or in a sprint from a small group.

But Pogacar’s approach has transformed the race:

• He now attacks earlier on the Cipressa.

• UAE Team Emirates makes the race extremely hard before the Poggio.

• Pure sprinters are increasingly eliminated earlier.

Even Van der Poel acknowledges this change, saying Pogacar’s aggression has shifted the key point of the race to the Cipressa.

This means Milan–San Remo is no longer simply a waiting game for the final climb.

2. Van der Poel Remains the Perfect San Remo Rider

Van der Poel has a rare combination of:

• explosive climbing

• tactical positioning

• elite sprint

This makes him uniquely suited to Milan–San Remo.

In 2025 he managed to:

• survive Pogacar’s attacks

• descend perfectly

• win the sprint

It was his second victory in the race, confirming his dominance in this Monument.

3. Pogacar Still Has One Weakness

Pogacar is arguably the strongest rider in the world, but Milan–San Remo remains elusive.

He has come close several times but still hasn’t won the race.

The problem is simple:

• Pogacar must drop Van der Poel before the finish

• If Van der Poel reaches San Remo with him, the Dutchman is favourite in a sprint.

That tactical reality will again define the race.

The Key Attack Points in Milan–San Remo

Despite being nearly 300 km long, the race almost always explodes in the final 30 km.

Here are the most likely decisive moments.

1. Cipressa (22 km to go)

The Cipressa is now arguably the most important climb in the race.

• Length: ~5.6 km

• Gradient: ~4–5% average

Although not extremely steep, the climb comes after 260 km of racing, making it devastating if ridden at high speed.

Likely scenario

Expect UAE Team Emirates to set a brutal pace before Pogacar attacks near the summit.

If Pogacar can:

• drop Van der Poel

• or create a small elite group

the race could already be decided here.

2. Descent of the Cipressa

The descent is technical and fast.

This is where riders like:

• Van der Poel

• Matej Mohorič

• Tom Pidcock

can gain time with aggressive descending.

If Pogacar attacks on the Cipressa but the group regroups on the descent, the race resets for the Poggio.

3. Poggio di San Remo (5 km to go)

The Poggio is the final climb.

• Length: 3.7 km

• Average gradient: ~3.7%

It’s not steep, but the pace is ferocious after nearly 300 km.

This is where Pogacar launched multiple attacks in 2025.

Likely scenario

Pogacar will almost certainly attack again here.

If he gains even 5–10 seconds at the summit, it could be enough.

4. Poggio Descent

The descent into San Remo is extremely technical.

Great bike handlers can win here:

• Mohorič famously did it in 2022

• Van der Poel is also excellent downhill

A small gap at the top of the Poggio can become decisive.

Other Contenders for 2026

While Pogacar vs Van der Poel dominates the headlines, several riders could upset the duel.

Filippo Ganna

• Time-trial power

• Strong enough to follow the climbs

• Nearly won in 2025

Wout van Aert

• Elite classics rider

• Strong sprint from a reduced group

Mads Pedersen

• Survives climbs well

• Very fast finisher

Matej Mohorič

• One of the best descenders in the peloton

• Always dangerous on the Poggio descent

Form Guide Ahead of Milan–San Remo 2026

Recent racing suggests Van der Poel is arriving in strong form.

• He has already taken stage wins at Tirreno–Adriatico.

• His performances suggest he is peaking for the Classics.

• Pogacar also enters the race as one of the favourites again.

Predicted Scenario for Milan–San Remo 2026

Based on recent editions, the likely script is:

1. Early breakaway survives until the Tre Capi.

2. UAE sets a brutal tempo approaching the Cipressa.

3. Pogacar attacks on the Cipressa.

4. Van der Poel follows.

5. Small group reaches the Poggio.

6. Pogacar attacks again.

7. If Van der Poel survives → sprint in San Remo.

Prediction

If the race finishes with Van der Poel still in the lead group, he remains the favourite.

But if Pogacar finally manages to drop him on the Cipressa or Poggio, the Slovenian could take his first Milan–San Remo victory.

Possible podium (prediction)

1. Mathieu van der Poel

2. Tadej Pogacar

3. Filippo Ganna