Akinwande began his career with Millwall at the age of seven, and remained at the club for nine years. After his release by Millwall, Akinwande signed for Conference Premier side Dartford in the summer of 2013. Akinwande made three brief substitute appearances in three different cup competitions during his first season at Dartford. He first appeared in their 1–0 win against Charlton Athletic in the Kent Senior Cup on 17 October 2013, and then, after making his Dartford league debut as a late substitute in their 1–0 home defeat against Forest Green on 12 April 2014, Akinwande was promoted to Dartford's first-team squad ahead of the 2014–15 season. During the summer of 2014, Akinwande had trials with Brentford and Crystal Palace. He first lined up for Brentford a pre-season friendly in late July, and played a part in their 2–1 victory over Maidenhead United for the club's Development Squad. A few days later, he was included in the Crystal Palace under-21 squad in a 3–2 victory at Dulwich Hamlet for another friendly. Remaining with Dartford for the 2014–15 season, Akinwande was one of four players loaned to Isthmian League Division One South club Walton Casuals. Despite failing to make an appearance for the club during his short spell, Akinwande was loaned to Isthmian League Premier Division side Leatherhead for a month in November 2014. He played for the club on six occasions during the month, four times in the FA Trophy, once in the Isthmian League Cup, and once in the Surrey Senior Cup. Akinwande left Dartford to sign for Fisher in January 2015. He made his debut on 5 January in their 3–1 defeat by Tunbridge Wells in the Southern Counties East Football LeagueChallenge Cup and scored his first goals during a 2–2 league draw with Phoenix Sports on 8 March. He went on to score four goals in total in 13 league and cup appearances. Akinwande left Fisher at the end of the season to join Isthmian League Division One North side Maldon & Tiptree. He scored on his debut for the Jammers on 8 August 2015 in new manager David Wright's first game in charge as they won 2–1 against Phoenix Sports. He scored four goals in his first five games for the club, going on to score eleven goals in 15 league games and twelve in 18 games in all competitions.
Colchester United
Akinwande's performances for Maldon & Tiptree earned him a trial with League One side Colchester United's Academy where he featured in two games for the Development Squad in November 2015. He signed a professional contract with the club until the end of the 2015–16 season, remaining in the Development Squad. In February 2016, Akinwande was named in the first-team squad for the first time. He was handed shirt number 16 and was an unused substitute in Colchester's game against Bury on 20 February. He was handed his professional debut on 12 March when manager Kevin Keen named Akinwande in his starting eleven to face Wigan Athletic at the Colchester Community Stadium. He played the first 45-minutes in the 3–3 draw before being replaced by Gavin Massey. He was offered a new contract by Colchester at the end of the season. He agreed a new one-year deal with Colchester on 7 July 2016. On 21 October 2016, Akinwande joined National League South side Bishop's Stortford on loan for one month. He scored on his debut on 22 October as Stortford lost 5–1 at home to St Albans City. He scored three goals in seven league outings, and six goals in ten games in all competitions. Akinwande made a loan return to Maldon & Tiptree on 3 February 2017, signing for an initial one month. He made his second debut for the Jammers on 4 February in their 1–0 defeat at Brightlingsea Regent, and scored his first goal in his second match during a 4–0 win over Thurrock on 11 February. On 3 March 2017, Akinwande joined National League South club East Thurrock United on a one-month loan. He scored four goals in six league appearances. He ended the 2016–17 season with one League Two appearance for Colchester. He was released by the club in May 2017 after they decided to not offer him a new deal.
Return to non-League
Akinwande rejoined East Thurrock United in the summer of 2017 following his Colchester release. After eight appearances and just one goal for East Thurrock, Akinwande signed for league rivals Concord Rangers.
