In 2006 the youngster was spotted by the Latvian Higher League club FK Rīga and Čekulajevs signed his first professional contract.
Soon he left the team, going abroad for the first time in his career and joining FK Náchod-Deštné in the Czech Fourth Division.
He started the 2009 Latvian Higher League season with them, but after 6 matches without scoring any goals, left for Víkingur Ólafsvík, playing in the Icelandic 2. deild karla.
By the end of the season, he had scored 46 goals in 35 appearances, not only being the top scorer of his team and the league, but also setting a new goalscoring record for the division.
[8] In June 2012 he was named the third top scorer in Europe by the UEFA league point system, thanks to his 46 goals, coming after Cristiano Ronaldo (46) and Lionel Messi (50).
[14] Čekulajevs didn't join any of the previously mentioned teams, signing a contract with the Maltese Premier League champions Valletta F.C.
[18] On 3 July 2012, Čekulajevs moved to the Hungarian Nemzeti Bajnokság I, as a free agent signing a contract with Lombard-Pápa TFC.
On 8 March 2013, it was announced that Čekulajevs had moved to Thai Division 1 side TTM Lopburi on a free transfer, signing a one-year contract.