Anan Khalaili

Khalaili joined the academy of local side Beitar Haifa in 2012, spending two seasons before a move to Maccabi Haifa. After a number of seasons with Maccabi Haifa, he spent the 2019–20 season with the Neve Yosef academy, where he scored twenty-five goals in twenty-four games, prompting Maccabi Haifa to recall him. His father, who worked as a coach at Neve Yosef, stated that Maccabi Haifa had initially expected Khalaili to spend two seasons with the academy, but due to his performances, they requested him back after only one season.

Maccabi Haifa

On 2 February 2022, Khalaili made his senior debut in the 2–0 win against Hapoel Hadera in Israel State Cup competition. On 11 July 2023, he scored his debut goal for the senior team in the 4–0 win against Ħamrun Spartans in UEFA Champions League qualifying.

Union SG

On 3 April 2024 signed for the Belgian Pro League club Union SG. He contributed to their first Belgian Pro League title in 90 years during the 2024–25 season. He featured in the 2026 Belgian Cup final as his club secured a 3–1 win over Anderlecht after extra time. On 9 December 2025, he scored his first UEFA Champions League goals by netting a brace in a 3–2 defeat against Marseille. On 13 July 2026, Khalaili's move to Inter Milan collapsed after he failed mandatory medical tests in Italy. The examinations, supervised by CONI, found irregularities that prevented him from receiving clearance to play in Serie A. Inter president Giuseppe Marotta stated…

Khalaili played for the Israel national under-20 team during the 2023 FIFA U-20 World Cup campaign. During the tournament, he scored the game-winning goal against Uzbekistan and scored the third and final goal of the game against South Korea. Khalaili made his senior international debut on 15 November 2023 against Switzerland in a 1–1 draw.

Khalaili is a versatile two-footed right sided player who was mainly a winger in his time at Maccabi Haifa, but after he moved to Union SG, depending on the formation, he transitioned into an effective wing-back. He has also occasionally been deployed as a forward, where he was a prolific goalscorer in his youth days. Khalaili is known for his work rate, dribbling and tactical versatility, combining close ball control and progressive ball carrying with defensive discipline, while creating chances through crosses and key passes.

Anan Khalaili was born in Haifa, Israel, to a Muslim-Arab family who moved there from the Arab town of Sakhnin, Israel. His father Majdi Khalaili is a former footballer, who used to play as a goalkeeper. His younger brother Iyad Khalaili is also a footballer who plays for Israeli Premier League club Maccabi Haifa.