Benayoun blossomed at Maccabi Haifa at club and international level. He was voted Player of the Year as Maccabi won their first title in seven years in the 2000/01 season, and a year later triumphed in the League again. In 2003, the midfielder was on his way to northern Spain and Racing Santander. Benayoun starred in a struggling Santander side and established a good reputation that Rafa was very aware of. After 101 league appearances and 21 goals, Santander was forced to cash in because of financial dire straits. West Ham parted with £2.5million for the Israeli playmaker in the summer of 2005. He scored five goals and made seven assists as the Hammers finished a respectable ninth in the 2005/06 season and reached the FA Cup final. Benayoun proved very tricky for Liverpool's defence and his performance certainly played its part in Rafa signing him a year later.

Benayoun's first season at Anfield can certainly be described as successful as he featured in 47 of Liverpool's 59 competitive matches but was introduced as a substitute 21 times which must have been frustrating. Benítez felt he was a match-winner but more often than to Benayoun's liking he didn't have a place for him in the starting line-up. Still, eleven goals was a more than satisfactory figure for a man playing as a second striker and included hat-tricks against Besiktas in the Champions League and Havant & Waterlooville in the FA Cup. He had a knack of being 'in the right place at the right time' because no fewer than three of those six goals came when he reacted quickly to shots by his colleagues that had been saved or blocked.

Benayoun made further progress in his second season as Liverpool made a championship challenge. His skill on the ball was a joy to behold and his vision second to none but he was still considered mainly an impact player. He scored nine times from 42 first-team appearances in the 2008/09 season and signed a two-year extension to his contract binding him to the club until 2013. Benayoun had another steady season in 2009/10 starting 29 competitive matches but significantly being replaced in 22 of them. His hat-trick in the early-season Anfield encounter with Burnley was a unique treble in another way too, making him the only English-based player to have scored hat-tricks in the Premier League, the Champions League and the FA Cup.

Ironically Benayoun's best-ever form in a Liverpool shirt, when he played more regularly in the second half of the 2009/10 season, was rewarded with a transfer to Chelsea in the summer of 2010! His move came as a surprise to say the least and Benayoun explained why he left: "There is only one reason - Rafa Benítez. I want Liverpool fans to know the truth and for them to know I made up my mind to leave a long time ago because of Benítez. He never treated me with the respect I deserved." Benayoun's first season back at a London club since 2006/07 was definitely one to forget. A serious Achilles injury kept him out of action for over half the season and although he eventually made a good recovery he only played in seven Premier League matches for Chelsea. Benayoun was loaned to Arsenal in the 2011/12 season where he played 26 first-team matches, scoring six times. The 32-year-old Benayoun made another loan-move, this time back to one of his former clubs, West Ham United, in the summer. He only made four starts at the Hammers and returned to Chelsea at the end of December 2012.

Benayoun, who reached his 33rd birthday shortly before the end of the 2012/13 season, made only six Premier League appearances for Chelsea once he had returned to Stamford Bridge from his loan spell at West Ham. Benayoun became a free agent in the summer of 2013. On 10 December 2013 Benayoun moved to Queens Park Rangers for the remainder of the 2013/14 season. Sixteen league appearances and three goals show that the short-term deal with Rangers was beneficial for both the player and the club. Rangers reached the Championship play-off final as they sought to make an immediate return to the Premier League but it was unclear at the time of that final whether the Israeli, who passed his 34th birthday shortly before the end of the 2013/14 season, would be seeking a new contract with Rangers or any other club.

On 6 June 2014, it was announced that the 34-year-old midfielder had agreed a two-year contract with one of his former clubs, Maccabi Haifa. He then joined Maccabi Tel Aviv in the summer of 2016 but only found the net once. For 2017/18 he was with Beitar Jerusalem but lost his place in the second half of the season. At the beginning of 2018/19, he joined Maccabi Petah Tikva, then moved back to Beitar in the January transfer window. He announced in April 2019 that this would be his last season as a player and in his final game on 4 May, he captained Beitar in a 3-2 home defeat to Ashdod. Benayoun's five children were at the game, each wearing a shirt of the five different clubs he had played for in England.