Tadej Pogačar's final challenges: A fifth Tour de France title – It feels like an inevitability

This is the final part in a mini-series exploring five of the major achievements missing from Tadej Pogačar's already stunning palmarès: Milan-San Remo, Paris-Roubaix, the Vuelta a España, an Olympic title, and a record-equalling fifth Tour de France title.

Can he tick these off? We've taken a closer look at each race to analyse his chances.

Tadej Pogačar is going to go down as one of the greats. Not just of his generation, but one of the best cyclists ever. Even if he hung up his wheels tomorrow, the things he has achieved by 27 put him in that category already; that much is clear.

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However, there are still a few clubs he has not yet entered, and achievements that would cement him as truly comparable to the sport's greatest ever winners. One of those, and perhaps the most obvious next club for him to join, is the group of five-time Tour de France winners.

No rider has officially ever won more than five – Lance Armstrong of course, 'won' seven, but has been stripped of those titles due to doping – but four riders are currently tied on five. Those four are Eddy Merckx, Bernard Hinault, Miguel Indurain, and Jacques Anquetil - all riders who are widely regarded as greats. Pogačar currently has four Tour de France titles, the same number as Chris Froome.

Whether he will say it or not – Pogačar is historically not keen on setting out records to break – it seems obvious that the Slovenian would want to at least join the 'Five Club'. Without getting ahead of ourselves, it doesn't seem crazy to suggest that he could even go above and beyond and win a sixth title, given he only just turned 27. Chris Froome was 28 when he won his first Tour, let alone the rest.

So, even if the answer seems pre-determined, let's dive a little deeper into how and when Pogačar might win Tour number five.

Three in a row in 2026

The next chance Pogačar has to win his fifth Tour de France is this coming July, and whilst he's yet to formalise his plans for 2026, we're fairly sure his season is going to be built around the Tour, as it has been for the last several seasons. It seems like one day he might pivot away to perhaps target the Vuelta a España, or go bigger on his Classics campaign, but for 2026, it's likely to be about the Tour once more.

Having seen the full route, and knowing who he's up against, and with the race less than seven months away, it doesn't feel pre-emptive to say that yes, Tadej Pogačar has a pretty good chance at winning the Tour de France in 2026, and becoming the fifth rider to take five yellow jerseys.

At this year's Tour, he was untouchable even when racing through a knee injury, and he has shown no signs of slowing down; in fact, 2025 felt like his best season yet. He's already the favourite for the Tour, and it seems more likely than not that he will win Tour number five this coming July. There's really no two ways to say that, even if it doesn't feel that exciting to be already predicting the winner of the biggest race of the year.

Of course, Pogačar has been beaten at the Tour twice, by a truly impressive Jonas Vingegaard, who is not to be underestimated. I'm the last person to brush over Vingegaard's achievements, or rewrite history to say that Pogačar is unstoppable at the Tour. He definitely isn't.

But, at the moment, it does feel like the balance of power has shifted back towards Pogačar. He's won two in a row again, he's getting stronger in other races, UAE are solid and boast ever-improving domestiques. The once-imperious Vingegaard has had setbacks and wobbles, Visma have lost some key domestiques. It's not to say the Danish rider can't return to the place that saw him trump Pogačar not once but twice, but as things stand right now, the Slovenian is on top.

Of all the remaining challenges we've talked about in this series so far, the achievements that would really round out Pogačar's astonishing achievements and really cement his place in the cycling canon, this one feels the most dead set. It's not a race he's tried to win before and hasn't, like Roubaix or San Remo, it's not something he'd have to rearrange his season for like the Vuelta, and it's not something there's only one chance of, like the Olympics.

Winning the Tour is something Pogačar has done four times already, he knows how to do it, he knows how to beat every rider he'll be up against next July. Of course, injury or illness or other forces majeures could throw things of course, but as it stands now, Pogačar becoming a five-time Tour winner feels like a when (with a pretty likely answer of next year), not an if.

A record-breaking sixth?

Cycling is terribly fickle, and things can change very quickly, but based on Pogačar's current level, I don't think it's crazy to float the idea that he could go even further than equal the Tour record – he could actually break it.

Winning a sixth Tour is not beyond his capabilities, given his age and the way he's been able to spread his Grand Tour-winning ability from 2020 until now already. There's no obvious reason or precedent as to why he might not still physically be able to win in just over 18 months' time.

There are, of course, challenges and external factors. Teams have tried, and are trying, to break him. We know that Vingegaard can beat him over three weeks, since he's done it convincingly twice already, and Red Bull-Bora-Hansgrohe are putting a lot into their project to try and win the Tour, be it with Remco Evenepoel or Florian Lipowitz. There's also the matter of the route – heavy TTing, or another innovation from ASO, could always scupper his plans. But really, all these challenges feel fairly surmountable, should he win number five and want to go for number six.

The main thing standing in Pogačar's way, then? Probably himself. He's made it clear that he sometimes tires of the unique pressures of the Tour, and has even sometimes seemed to be lacking in enjoyment and excitement at the race. Whether he wants to put himself through the rigour involved with trying to win the same race for the sixth time remains to be seen. Maybe he will want to focus one year on trying to win Roubaix and Milan-San Remo instead, and forget about the Tour.

But come on. An out-and-out record is on the line. If he goes into 2027 with five wins, and he's fit and healthy and not totally burnt out yet, surely he has to go for it. And it would not surprise me at all to see him become the first rider to win six Tours de France. He's a generational rider, and he could have the chance to do something truly astronomical. I can't see him passing that up if he gets the opportunity to try.

What do you think? Will Pogačar win Tour number five, or even six? Let us know your thoughts in the comments below.