Jake is a Football and Entertainment betting expert, with a Man City season ticket and a deep knowledge of reality TV betting angles
- Harry Styles leads early Glastonbury 2027 headliner speculation at 2/1.
- Sam Fender, Taylor Swift, and Fred Again also feature prominently in our expert odds.
- The next Glastonbury will take place in 2027 following a 2026 fallow year.
Harry Styles Leads Early Betting Market Ahead of 2027
With Glastonbury 2025 now wrapped and the festival set to take a break in 2026, all attention has turned to who could grace the Pyramid Stage in 2027.
Following a packed 2025 line-up featuring The 1975, Neil Young, and Olivia Rodrigo, the 2027 edition is already shaping up to be one of the most anticipated returns in Worthy Farm history.
The fallow year in 2026 means festival-goers will have to wait two years for the next Glastonbury and with that anticipation comes speculation.
Music insiders and fans alike are already discussing who might headline the festival’s comeback, with our experts pricing up a hypothetical early market based on rumours, album cycles, and prior links to the festival.
| Glastonbury Festival 2027 Headliner | Odds* | Probability |
|---|---|---|
| Harry Styles | 2/1 | 33.3% |
| Sam Fender | 3/1 | 25.0% |
| Taylor Swift | 4/1 | 20.0% |
| Fred Again | 5/1 | 16.7% |
| Madonna | 6/1 | 14.3% |
| Green Day | 7/1 | 12.5% |
| Red Hot Chili Peppers | 7/1 | 12.5% |
| Muse | 8/1 | 11.1% |
| Oasis | 8/1 | 11.1% |
*These odds are hypothetical and created by our experts purely for entertainment purposes.
What the expert says...
Big names follow in the market
Harry Styles is currently the 2/1 favourite, with speculation suggesting his next album cycle and continued global success make him a prime candidate.
After skipping Glastonbury despite strong rumours in recent years, 2027 could be the right time.
Sam Fender at 3/1 is seen as a realistic homegrown option after growing his live reputation massively across UK festivals, while Taylor Swift, who was booked to headline Sunday night at the 2020 edition that was cancelled due to the pandemic, sits at 4/1. A long-awaited Glastonbury appearance from Swift would undoubtedly be a major draw.
Entertainment Betting Sites: Best Bookmakers Compared on Reality TV, Entertainment and Novelty Bets
Where to Bet on Entertainment Markets
While these Glastonbury 2027 headliner odds aren’t currently available with UK bookmakers, similar entertainment specials often are.
Fans looking to bet on music and pop culture markets can visit the best entertainment betting sites, where free bets are frequently offered for major specials, TV events, and awards ceremonies.
Keep an eye on leading betting sites as 2027 nears and official rumours begin to solidify.
