Milan San Remo 2021 Betting


The first monument of the 2021 cycling season gets underway this Saturday, March 20th, as some of the sport’s top stars head to Italy for the longest one-day classic known as the Milan-San Remo.

This will be the 112th edition of the race, which first began in 1907. The Milan-San Remo is also considered a sprinters race as it’s a mostly flat course that spans 185.5 miles (299km).

?La prima Classica Monumento della stagione non si scorda mai!
Chi taglierà̀ per primo il traguardo della Milano-Sanremo presented by @eolo_it quest’anno? | The first Classic Monument of the season cannot be missed. Who is going to win the 2021 Milano-Sanremo presented by EOLO?

— Milano Sanremo (@Milano_Sanremo) March 15, 2021

The 2021 Milan-San Remo Route

As always, this race will begin in Milan and finish in San Remo. For the most part, this year’s route will remain the same. However, there is one notable change.

The usual Passa del Turchino climb has been blocked by a landslide and was not available for this race. So, organizers replaced it with the Colle del Giovo. There will be 112km remaining after this new climb, which comes a little past the halfway mark.

The final 20km remains unchanged as riders will fly up the Cipressa and the Poggio before descending towards a final 2.2km of flat road which will be filled with vicious sprints.

Previous Milan-San Remo Winners

The first Milan-San Remo was held in 1907 and won by Lucien Petit-Breton. Since then, the great Eddy Merckz won the most Milan-San Remo races with seven. Wout van Aert is the reigning race winner.

The following is a list of winners dating back to 2011:

2011: Matthew Goss
2012: Simon Gerrans
2013: Gerald Ciolek
2014: Alexander Kristoff
2015: John Degenkolb
2016: Arnaud Demare
2017: Michal Kwiatkowski
2018: Vincenzo Nibali
2019: Julian Alaphilippe
2020: Wout Van Aert

? I love that the longest race of the year sees some of the tightest finishes. #MilanSanremo

— daniel (@cyclingreporter) March 16, 2021

Milan San Remo Betting Odds

The following odds are courtesy of Bovada:

Mathieu Van Der Poel (+250)
Wout Van Aert (+400)
Julian Alaphilippe (+650)
Sam Bennett (+1000)
Davide Ballerini (+1400)
Michael Matthews (+1600)
Arnaud Demare (+2200)
Caleb Ewan (+2500)
Primoz Roglic (+2500)
Matej Mohoric (+2800)
Alexander Kristoff (+3300)
Fernando Gaviria (+3300)
Filippo Ganna (+3300)
Mads Pedersen (+3300)
Pascal Ackerman (+3300)
Philippe Gilbert (+3300)
Soren Kragh (+3300)
Giacomo Nizzolo (+4000)
Greg Van Avermaet (+4000)
Ivan Garcia Cortina (+4000)
Jasper Philipsen (+4000)
Nacer Bouhanni (+4000)
Christophe Laporte (+5000)
David Dekker (+5000)
Elia Viviani (+5000)
Jasper Stuyven (+5000)
Michal Kwiatkowski (+5000)
Oliver Naesen (+5000)
Gianni Moscon (+6600)
Magnus Cort Nielsen (+6600)
Matteo Trentin (+6600)
Sonny Colbrelli (+6600)
Tadej Pogacar (+6600)
Vincenzo Nibali (+6600)
Alex Aranburu (+8000)
Jake Stewart (+8000)
John Degenkolb (+8000)
Anthony Turgis (+10000)
Bryan Coquard (+10000)

Milan San Remo Betting Favorites

Mathieu Van Der Poel (+250)

Van Der Poel has already had a good start to his 2021 season so far. He won Strade Bianche and also took two stages in Tirreno-Adriatico which helped him finished 3rd in the points classification.

?? Mathieu van der Poel wins the ?? Strade Bianche!

What. An. Attack. ??

— (@cyclocross24) March 6, 2021

He’s only competed in this race one time before and that came last year where he finished 13th overall.

Van Der Poel is one of the biggest rivals to Wout Van Aert and if he’s on top form then he will be very tough to beat this Saturday.

Wout Van Aert (+400)

WVA finished 4th in Strade Bianche, which was his first race of the season. He followed that up with a strong showing in the Tirreno-Adriatico where Van Aert finished 2nd in the general classification behind Tadej Pogacar.

Yet, he won the points classification and two stages. His most impressive performance at the Tirreno-Adriatico might have been on Stage 7 where he won the individual time trial. WVA finished the race with five Top 3 finishes.

This will be the 3rd time WVA has competed in this race. He was 1st last year and 6th in 2019.

Van Aert looks in good form and aims to win the Milan-San Remo for the second straight year. The last time a rider won this race in consecutive years was Erik Zabel in 2000-2001.

Julian Alaphilippe (+650)

Like a hilly stage, Alaphilippe has had an up and down 2021 season so far. He was 2nd overall in the Tour de la Provence in February, but followed that up with a 57th at Omloop Het Nieuwsblad.

Julian then bounced back for a 2nd place result at Strade Bianche where he finished behind Van Der Poel, but ahead of Wout Van Aert and Egan Bernal.

At the Tirreno-Adriatico, Alaphilippe won Stage 2, but wasn’t a factor the rest of the race. Now, he turns his attention towards Milan-San Remo which he won in 2019.

This will be his 5th overall appearance. In 2017, Julian was 3rd. His second run at this race ended in a 35th place result. Last year, Alaphillipe finished 2nd behind Van Aert.

The final 20km of this race are perfect for a punchy rider like Alaphilippe. But, will he have enough to outsprint Van Aert and Van Der Poel?

Sam Bennett (+1000)

Speaking of sprinters, Sam Bennett is arguable the top sprinter right now. At least that can be said for stage races as other sprinters might be slightly faster.

Bennet had strong showings in both the UAE Tour and Paris-Nice. He finished 2nd in the points classifications for both stage races.

At the UAE Tour he won two stages and finished runner up on another. At Paris-Nice, he also won two stages.

Julian Alaphilippe and Sam Bennett lead Deceuninck-QuickStep at Milan-San Remo

— (@Cyclingnewsfeed) March 17, 2021

This will be Bennett’s 6th time competing in the Milan-San Remo. He’s on the same team as Julian Alaphilippe, so he could end up being more of a supporter than going for his own glory.

In his previous five appearances, Bennett’s best result was 28th in 2019. He was 60th in last year’s race. I would avoid Bennett this weekend as he will get dropped on the punchy hills near the end of the race.

Davide Ballerini (+1400)

Another teammate of Alaphilippe is Ballerini who’s a native of Italy. He’s raced well this season and could be a sneaky pick if his teammates struggle at all.

Ballerini won two stages in the Tour de la Provence last month, which resulted in a victory of the points classification. He followed that up with a win at Omloop Het Nieuwsblad.

However, he then tallied two straight DNFs before a decent showing at Tirreno-Adriatico where he was 8th in the points classification.

This will be Ballerini’s 3rd appearance in the Milan-San Remo. He finished 140th in 2017 and 19th in 2019.

I like his chances better than Bennett’s, but Alaphilippe is the man for Deceuninck – Quick Step which means I would also avoid taking Davide Ballerini this weekend at online betting sites.

The Best Milan San Remo Betting Value

Michael Matthews (+1600)

Matthews had quite the 2020 season where he finished a four year stint with Team Sunweb in a bit of controversy. He was sent home during the middle of the Giro d’Italia for a false positive covid test. It really highlighted his rocky relationship with the team.

Live on @SBS + @SBSOnDemand
right now!

Can Michael Matthews take the win on this very lumpy course?

All to play for out on the road as the riders take on what promises to be a fun stage!

Link: #couchpeloton #ParisNice

— CyclingCentral (@CyclingCentral) March 12, 2021

This year, Matthews has returned to an Australian team that he raced for earlier in his career. Matthews made the following comments about racing for a new team in 2021:

“It’s good to be starting my season. It’s been a long build-up, from having a false positive in the Giro last year to being here now as the start line of Paris-Nice, back with GreenEdge and with BikeExchange. To be honest it feels like I’m coming back home. All of the guys are pretty much the same. We’ve got a couple of new guys, but still a lot of Aussies, and the staff is still the same and, in a way, it feels like I haven’t been away.”

A happy Matthews means a more dangerous rider on the course. His first race of the 2021 season was Paris Nice where he had two third place stage results and a 4th in the points classification. These are good results for his first event this year and on a new team.

For Matthews, this will be his 9th appearance. He knows this race very well and finished 3rd here last year. That tied his career best mark which was first set in 2015. This will be the 8th straight year that he’s competed in this race.

I like his chances better than everyone other than Alaphilippe, Van Aert and Van der Poel. At +1600, Michael Matthews offers solid value.

Arnaud Demare (+2200)

The French sprinter has competed in three events this year with decent results. He had two runner ups on stage finishes in the Tour de La Provence and Paris-Nice. He also cracked the Top 10 for points classifications in both stage races.

For Demare, this will be his 9th appearance in the Milan-San Remo. He won this race in 2016 and was 3rd in 2018. However, the last two years haven’t been as kind. Demare finished 32nd in 2019 and 24th in 2020.

As a former winner, these odds offer value. But, he will need some luck to beat out the race favorites.

Caleb Ewan (+2500)

The Australian sprinter pulled out of the Tirreno-Adriatico on Stage 3 because he wasn’t feeling well. He finished second in the Stage 1 sprint as Wout Van Aert edged him out at the line. Stage 2 saw Ewan finish 164th and eventually lead to the decision of pulling out of the race.

The ream released a statement saying that Ewan wasn’t feeling well and wanted to rest up for the Milan-San Remo:

?? #TirrenoAdriatico

It’s a close second for @CalebEwan in a thrilling sprint!

— Lotto Soudal (@Lotto_Soudal) March 10, 2021

“Caleb Ewan has withdrawn from the race as he has been suffering from mild gastro-enteritis. The decision to abandon was taken in order to not jeopardize his participation at Milan-San Remo this coming Saturday.”

Prior to the Tirreno-Adriatico, Ewan competed in the UAE Tour where he won Stage 7. It was his first and only win of the year.

This will be Ewan’s 5th appearance in the Milan-San Remo. His best result came in 2018 when he finished 2nd. Last year, Ewan was 113th overall.

Ewan is one of the fastest sprinters in the field. But, he will need to be 100% healthy and get a little bit of luck to have a shot at winning on Saturday. Yet, his odds do offer small value.

Alexander Kristoff (+3300)

Kristoff’s 2021 season hasn’t been one to brag about. He has yet to win a stage or a race and has competed in four events so far. His best result was 6th on Stage 5 of Paris-Nice. Kristoff is hoping he can recapture some of his old magic and compete for another Milan-San Remo win.

This will be Kristoff’s 10th appearance in the Milan-San Remo. He won this race in 2014 and was runner up in 2015. Since then, he’s had two 4th place results as well. However, he was 83rd last year.

There’s small value with Kristoff as he definitely has the experience to win again. But, does he have the legs to compete with the race favorites?

The Best Longshot to Win the Milan San Remo

Michal Kwiatkowski (+5000) will lead Team Ineos into this monument race where he’s had success at in the past.

In eight Milan-San Remo appearances, Kwiatkowski has one win and a podium finish. He won this race in 2017 and finished 3rd in 2019. Last year, he was 15th.

Although the Polish cyclist hasn’t had much success in 2021 so far, he does have the skills to win this race again. He will need some luck and great form to have any shot at winning on Saturday.

Top 3 Riders

The following odds are for a Top 3 finish and courtesy of DraftKings:

Mathieu Van Der Poel (-155)
Wout Van Aert (-143)
Julian Alaphilippe (+150)
Sam Bennett (+300)
Davide Ballerini (+400)
Michael Matthews (+500)

I think that the Top 3 finishers for this year’s race will come from the six cyclists above. All six of them offer betting value based on their odds and their overall success in monument races.

I see Van Der Poel and Van Aert being locks for two of the Top 3 results. The third cyclist will most likely be Alaphilippe, but I can also see Michael Matthews edging out the French star if Julian is not 100%.

As of now, play it safe and take Van Der Poel, Van Aert and Alaphilippe as the Top 3 riders on Saturday.

Who Wins the 2021 Milan San Remo?

The 112th edition of the Milan-San Remo is going to be an exciting race because of the talented cyclists involved in the event.

As mentioned above, Mathieu Van Der Poel, Wout Van Aert and Julian Alaphilippe are my picks to finish in the Top 3. The race winner will certainly come from this trio.

? Saranno loro i prossimi a contendersi la Classicissima? Julian Alaphilippe ? Mathieu van der Poel | ? Could they be the next to compete at #MilanoSanremo presented by @eolo_it?

@alafpolak ? @mathieuvdpoel

— Milano Sanremo (@Milano_Sanremo) March 13, 2021

Now, the hard part is trying to decide between these three fantastic riders. Of the trio, Alaphilippe seems to be lacking a little bit in 2021 compared to the others. So, I’m going to eliminate the French rider from winning this race.

In reality, you couldn’t ask for a better result than the finish coming from Van Der Poel or Van Aert. These two are rivals on the bike and will certainly make things exciting at the end of Saturday’s race.

We can look at how the two did in their most recent race, which was the Tirreno-Adriatico, and make our best guess based on these results.

Van Der Poel won two stages in the race and finished 3rd in the points classification. However, Wout Van Aert won the points classification, also won two stages, and finished 2nd overall in the general classification.

WVA might have finished behind MVDP at Strade Bianche, but he showed that he has the legs to win any race and offers better value to win the Milan-San Remo this weekend.

I’m taking one of my favorite riders Wout Van Aert to win this race on Saturday.

Pick: Van Aert

Odds: +400

$100 Could Win You…$500.00

Rick Rockwell

As a longtime freelance writer, avid sports fan, former athlete, and experienced sports bettor, Rick Rockwell has risen up the ranks at to become the self-professed “King of the Blog” in his first year with the site. …

View all posts by Rick Rockwell