# Olympiacos football transfer activity

> Live situation record from CLSTR: https://clstr.news/situations/20260902-olympiacos-football-transfer-activity
> Updated: 2026-09-04T15:04:39.000Z. Sources: 36. Developments: 3.

Olympiacos has finalized several key transfer moves, including the official signing of Jamaican winger Leon Bailey from Aston Villa. The 29-year-old attacker, who has 41 caps for Jamaica and previously played for Bayer Leverkusen and Genk, has signed a contract through June 2030 following successful medical and ergometric examinations. This move follows his recent loan at AS Roma and a failed attempt to join Hull City. Reports indicate Bailey was part of the Aston Villa squad that won the UEFA Europa League in the 2025-2026 season.

Bailey has integrated into the squad under manager José Luis Mendilibar, completing his first training sessions at the Rente facility and selecting the number 17 shirt. He has expressed excitement about the move, stating, “I am very happy that I will be wearing the red and white and I look forward to experiencing the atmosphere of the Karaiskakis stadium.”

Following these acquisitions, Olympiacos finalized its squad list for the UEFA Europa League League Phase, including new signings Armando Gonzalez, Leon Bailey, and Gustavo Puerta. However, players such as Dani García, Lorenzo Sipolone, Zoel Roca, and Balša Popović were excluded from the European list. Additionally, the club reached a transfer agreement with OFI involving Tiago Nous and Giannis Apostolakis, a deal estimated to be worth over 5 million euros to OFI.

## Claims

- Olympiacos has reached a verbal agreement with Aston Villa to sign Leon Bailey on a permanent transfer. (corroborated by 2 sources)
- The contract for Leon Bailey is expected to run until June 2029. (corroborated by 2 sources)
- Leon Bailey is traveling to Athens to undergo medical examinations. (corroborated by 2 sources)
- Olympiacos is in advanced negotiations to sign Tiago Nous and Giannis Apostolakis from OFI. (single source)

## Timeline

### 2026-09-04: Leon Bailey signs with Olympiacos through 2030

Olympiacos has signed Leon Bailey until 2030, while PAOK has submitted an offer for Polish goalkeeper Slawomir Abramowicz.

6 sources. https://clstr.news/cluster/leon-bailey-signs-with-olympiacos-fc-until-2030

### 2026-09-02: Leon Bailey joins Olympiacos from Aston Villa

Olympiacos has officially signed Jamaican winger Leon Bailey from Aston Villa on a contract lasting until 2030, following his successful medical in Athens.

34 sources. https://clstr.news/cluster/leon-bailey-linked-with-olympiacos-move-amid-al-ittihad-interest

### 2026-09-02: Olympiacos reaches transfer deal with OFI for Nous and Apostolakis

Olympiacos has reached a deal with OFI for players Tiago Nous and Giannis Apostolakis, worth over 5 million euros, with both players remaining at OFI on loan until their scheduled transfers.

8 sources. https://clstr.news/cluster/olympiacos-targets-leon-bailey-and-ofi-players-for-squad-reinforcement

---
Cite as: Olympiacos football transfer activity. CLSTR, https://clstr.news/situations/20260902-olympiacos-football-transfer-activity