[6] Following a series of impressive performances during the Kashif & Shanghai knockout competition in 2010, Trayon followed Guyana national team manager Jamaal Shabazz to Trinidad and Tobago to begin his professional football career for Caledonia AIA of the TT Pro League.
[8] The following months, Bobb scored in consecutive rounds during the TOYOTA Classic[9] and provided an additional two goals in an 8–0 win over Petit Valley United in the FA Trophy.
[10] 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.
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.
[24] Bobb opened the following season with an ankle injury suffered during preseason training that kept him sidelined for FK Kruoja's first eleven league matches.
On 8 May 2014, Bobb scored an 84th-minute goal in his debut for Kruoja during a league match against FK Dainava Alytus after coming as a substitute in the 66th minute.
[1] He began his international career for the under-20 team during qualification for the 2011 CONCACAF U-20 Championship, where Bobb made three appearances playing as a winger in wins over United States Virgin Islands and Grenada; and a loss to Jamaica.
In the second qualification round, Bobb scored his first goal for Guyana in the 81st minute against Netherlands Antilles, which resulted in the Golden Jaguars lone win in the group on 23 January 2011.
On 7 September 2013, Bobb scored a pair of goals on either side of half-time to earn the Golden Jaguars a 2–2 draw against El Salvador in Estadio Cuscatlán.
Bobb concluded an active year for the Golden Jaguars with six consecutive starts during Guyana's qualification attempt for the 2012 Caribbean Cup in October and November.