Obadeyi made his first team debut for Bolton as a substitute in the club's 0–1 home Premier League defeat by Wigan on 28 December 2008. In August 2009, Obadeyi signed for Swindon Town on a one-month loan and scored his first goal in a 2–1 victory over Southend United on 29 August. On 11 September his loan was extended by another month, and again on 15 October for a final month under the 93-day emergency loan limit. In January 2010, Obadeyi went on loan again, this time to Rochdale for the rest of the season. He scored his first goal for Rochdale against Dagenham & Redbridge on 20 February 2010. The third loan of his career was made on 22 October 2010 when he joined Shrewsbury Town on an initial one-month loan. On 24 November, the loan was extended until 8 January 2011, but following the end of that period, the club decided not to extend it any further. On 7 July 2011, Obadeyi signed a one-year extension to his contract at Bolton, and on 8 November joined League One team Chesterfield on loan until 26 December, making his debut the following day in a 4–3 win over Tranmere Rovers in the Football League Trophy. Obadeyi made his league debut for Chesterfield on 19 November in the 5–2 loss away to Oldham Athletic and made six appearances overall before returning to Bolton. On 14 March 2012 he began a second loan spell at Rochdale. The loan lasted a month and he scored once. However, at the end of the 2011–12 season, following Bolton's relegation from the Premier League, Obadeyi was released and subsequently joined Rio Ave at the start of June 2012. Obadeyi made 12 appearances in the Primeira Liga during the 2012–13 season without scoring as Rio Ave finished sixth in the league table. His one goal for the club came in December 2012 against Sporting CP in the Taça da Liga. Obadeyi left Rio Ave at the end of the campaign. He signed a one-year contract with Bury in August 2013. He played in two league games and one cup tie before joining Plymouth Argyle on loan in November until January 2014. Obadeyi made ten appearances for the club in all competitions during the loan, which was interrupted by a hamstring injury, and scored one goal against York City. On 20 February 2014, Obadeyi joined Plymouth Argyle for a second loan spell with the Devon club. Obadeyi established himself as Argyle's preferred choice on the left side of midfield, before his loan expired. He was released by Bury at the end of the season, Obadeyi signed a three-year contract with Scottish Premiership club Kilmarnock in July 2014. After two seasons with the club he signed for Scottish Championship club Dundee United in July 2016, joining on a one-year contract. On 31 January 2017, Obadeyi joined League One club Oldham Athletic on a contract until the end of the 2016–17 season. He was released by Oldham at the end of the 2017–18 season, following their relegation. On 25 July 2018, Obadeyi signed with Ligue 2 club Sochaux on a two-year contract.
