He made his professional debut in 2007 as a 17-year-old with his hometown club Besa, and would then go on loan to Skënderbeu, Tirana and South Korean side Incheon United between 2011 and 2012.

He joined Kukësi in 2013 and scored 22 goals in all competitions during the 2013–14 campaign, where he gained the attention of the Albania national team setup as well as Croatian side RNK Split who signed the player in 2014 for a reported fee of €100,000.

An Albanian international, Cikalleshi with 12 goals scored, is his country's joint active player top goalscorer along Armando Sadiku and 4th in the overall ranking.

Under Shpëtim Duro, Cikalleshi became a regular first team member during the 2009–10 campaign, where he was part of strike force that included Daniel Xhafaj and Vioresin Sinani, who are two of the most prolific strikers in Albanian football history.

[2] The 2009–10 campaign proved to be one of the club's most successful ever season, as they finished runners-up in the Kategoria Superiore behind Dinamo Tirana and won the Albanian Cup for only the second time in history.

He agreed to join Skënderbeu on a 6-month loan deal ahead of the opening of the January 1transfer window, and travelled with the rest of the squad to Antalya, Turkey for their mid season training camp.

[4][5] He made his debut for the club in the Albanian Cup against Bylis on 29 January, where he came on as a substitute in the 63rd minute for Klodian Duro in the goalless draw.

[11] Following FK Kukësi's elimination in the Europa League, on 16 July 2014 Cikalleshi signed for Croatian side RNK Split on a three-year contract for a fee of €100,000.

[14] On 6 June 2015, RNK Split accepted the €1.8 million bid of Turkish side İstanbul Başakşehir to transfer Cikalleshi to the Süper Lig club.

He made his debut few days later against Gümüşhanespor valid for the Turkish Cup playing as a starter in a 3–1 win with Akhisar Belediyespor progressing through the quarter-finals.

[21] In the next game week Cikalleshi gave 2 assist for all team's goals scored against Kasımpaşa in a 2–0 victory, which made Akhisar Belediyespor to secure standing in the Süper Lig for next season.

[28] On 16 January 2019, Cikalleshi made a surprise return to Turkish top flight by signing with Akhisar Belediyespor, whom he had a successful, albeit short spell in 2016–17 season.

[47] Later on 4 September 2010, with Albania already eliminated, Cikalleshi played his first match as starter in the final matchday against Azerbaijan, scoring a goal by unable to avoid the 3–2 away loss.

[49] After his good performances with Kukësi in the 2013–14 season, Cikalleshi received his first call up at the Albania senior squad by coach Gianni De Biasi for friendlies against Romania in May and Hungary & San Marino in June 2014.

[51] Cikalleshi lost his place in the starting lineup from the beginning of 2016 due to good running form of fellow striker Armando Sadiku.

In September 2017, he was called-up and later omitted by manager Christian Panucci for the matches against Liechtenstein and Macedonia as he asked permission to conclude his transfer at Osmanlıspor.