Andoni Iraola, Xabi Alonso and Mikel Arteta will be on opposing sides when Liverpool face Chelsea in the Carabao Cup on Wednesday night, before taking on Arsenal in the Premier League on Sunday

Three boys from the same Basque youth team are now going head-to-head in English football, but one of them was showing signs of his managerial future long before any of them dreamed of becoming Premier League bosses.

Andoni Iraola, Xabi Alonso and Mikel Arteta came through the ranks together at Antiguoko in San Sebastian during the 1990s, developing their talents at a club renowned for producing gifted footballers. Decades later, their journeys have taken them to some of the biggest dugouts in the game, with Arsenal, Chelsea and Liverpool now providing the backdrop to their reunion.

Liverpool face Chelsea in the Carabao Cup on Wednesday night before travelling to Arsenal in the Premier League on Sunday. Yet while all three managers share their Spanish heritage and formative years in the Basque Country, their early personalities offered very different clues about what lay ahead.

According to Roberto Montiel, a former Antiguoko coach who is now the club's vice president, Arteta stood out from the rest. The future Arsenal boss was already displaying the qualities of a budding tactician, studying training sessions and questioning his coach's decisions while still a youngster.

Montiel recalled that Arteta showed "a lot of maturity" for his age, regularly approaching him with suggestions about how to improve the team. On occasion, the youngster would even identify shortcomings in Montiel's own tactical approach.

"Mikel always played ahead of his age group and showed a lot of maturity despite being a little boy," he told The Sun. "Right away, we knew he could make it at a professional level.

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"He's the best player I have ever seen at Antiguoko, better even than Alonso, and I think he had the idea of being a coach a long time before he hung up his boots.

"Arteta would watch me coach some of the teams and afterwards bombard me with ideas and suggestions of how to change things around. He was still only young but I could see he was engineering the idea of coaching. I would laugh because he'd tell me where my team was failing and where I had to use the scalpel to make changes!"

Alonso, who would go on to enjoy the most successful playing career of the three, presented a different challenge for Montiel. Although "introverted" away from the action, the former midfielder had an authority on the pitch that commanded respect without the need for theatrics.

"Xabi was a small lad, who didn't bulk up until the Under-17s," Montiel said. "But he organised play very well and was a commanding presence without being very bossy."

"He was a bit introverted but transformed when on the pitch. He was never someone who needed to shout a lot - a few words was all it took. But he was always highly respected and when Xabi said something, everyone respected it."

Iraola, by contrast, was the quietest member of the group. He was a talented footballer and an accomplished student, but Montiel did not fully appreciate his potential as a coach until the former Athletic Bilbao defender returned to Antiguoko after hanging up his boots.

"Andoni was a very shy boy and a very good student, and he had spectacular talent," Montiel told the Liverpool Echo. "As a child, being very shy, when we had the game under control he would do things with the ball that very few players could do. We had a great team and I consider myself very, very competitive, and I instil that in all my teams."

Montiel would go on to help Iraola take his first steps into management, although he initially expected his former pupil to leave football behind altogether.

"The truth is that when he quit football, I thought he was going to retire, but when he called me and told me that he wanted to start coaching and asked if I could give him a team in Antiguoko, I saw that he might have the makings of a coach.

"He went to Madrid to get his coaching licence and there I saw that he might have a future, since he was the best in his class during the course."

Iraola began his senior managerial career with Cypriot outfit AEK Larnaca, spending one season there before returning to Spain in 2019 to take charge of Mirandes, who had recently earned promotion to the Segunda Division. A move to Rayo Vallecano followed a year later, providing the platform for his eventual rise in English football.

Bournemouth brought the Spaniard to the Premier League in 2023, and he quickly developed a reputation as one of the division's most exciting young managers. He led the club to new heights, including qualification for the Europa League, before Liverpool came calling in June and handed him the reins at Anfield.

Arteta's route into coaching was more straightforward. After retiring in 2016, he had three potential destinations: Arsene Wenger wanted him to lead Arsenal's academy, Mauricio Pochettino offered him a job in Tottenham's backroom staff after the pair had played together at PSG, while Pep Guardiola was ready to bring him into his Manchester City coaching team.

Arteta chose to work alongside Guardiola, beginning an apprenticeship that would prove crucial to his development. When Wenger departed Arsenal in 2018, the Spaniard emerged as a leading candidate to replace him, only for the club to turn to Unai Emery instead.

The opportunity eventually arrived 18 months later, when Arsenal dismissed Emery and brought Arteta back to north London. He has since overseen a remarkable transformation, taking the Gunners back to the top of English football and delivering a Premier League title.

Alonso took a different route again, returning to his homeland immediately after ending his playing career. He began coaching Real Sociedad B in 2019 before joining Bayer Leverkusen in 2022, where he established himself as one of the most highly regarded managers in Europe.

Leverkusen secured the first Bundesliga title in their history during the 2023/24 campaign, going through the domestic season unbeaten in a remarkable achievement that elevated Alonso's standing and attracted interest from some of the continent's biggest clubs.

A move to Real Madrid followed a year later, but his time at the Bernabeu ended before he could complete a full season. Chelsea subsequently appointed Alonso in July, bringing the three former Antiguoko team-mates together once more in the Premier League, albeit now as rivals in the managerial dugout.

Wednesday's meeting will see Alonso return to Anfield, this time in charge of the opposition. He received a warm welcome when he brought his Leverkusen side to Liverpool for a Champions League fixture in 2024, but the reception could be rather less friendly when he returns with Chelsea.