Bobb opened the 2012–13 season for Caledonia AIA as a starter in the "Stallions"' midfield. During the 2012–13 CONCACAF Champions League, he made two appearances for Caledonia during the group stage, including a start against Seattle Sounders FC of Major League Soccer on 2 August. In October 2012, Bobb was named the most valuable player of the First Citizens Cup after having set-up and scoring the winning goal to lead Caledonia AIA to a 2–1 win over Defence Force in the final. The following months, Bobb scored in consecutive rounds during the "TOYOTA Classic" and provided an additional two goals in an 8–0 win over Petit Valley United in the FA Trophy. On 8 January 2013, Trayon was one of five TT Pro League players invited for a two-week trial with a touring team in Turkey to play practice matches against several European clubs on their winter breaks. Before departing for Turkey, Bobb had made ten league appearances for Caledonia AIA in his two years with the club. On 21 February 2013, Bobb agreed to personal terms with TP-47 of Kakkonen, the third-level of association football in Finland. On 13 March, Bobb recorded his first career hat-trick in his debut for TP-47 during the third round of the 2013 Suomen Cup. He went on to make starting appearances the following two rounds before a defeat to TPV ended the Tornio club's run in the fifth round. Bobb recorded his first league goal in his debut for TP-47, on 28 April, to level the match against PK-37 at 2–2 in the 85th minute after scoring from a cross. A week later, Trayon scored his second goal in as many matches in a 2–0 win over Vasa IFK. He scored two more goals over the next five league matches against Tervarit on 19 May and a week later against KPV on 26 May. On 1 June, after scoring four goals in seven league appearances for TP-47, Bobb joined Veikkausliiga side RoPS on loan with the agreement to permit Trayon to compete for both clubs during the loan. The following day, Bobb became the first Guyanese to play in a Veikkausliiga match when he made his debut against FF Jaro coming on as a substitute for former Caledonia AIA teammate Ataullah Guerra in the 59th minute. Before returning to TP-47, Bobb made three Veikkausliiga appearances for RoPS.