Durojaiye joined Tottenham Hotspur at the age of seven and worked his way through the ranks up to the Under-18s as a striker.[1] After failing to be offered a professional contract, trialled with Cheltenham Town, Brentford and Oxford United before moving to Norwich City in August 2012.[2] He signed a one-year professional deal but was released at the end of the season.[3]
In July 2013, Durojaiye signed for Scottish Championship club Falkirk. He spent two seasons at the club before his release in May 2015.[4]
In February 2016, Durojaiye joined Hayes & Yeading United and began playing in a defensive role. After a short spell at Hungerford Town ahead of the 2016–17 season, he returned to Hayes & Yeading for a second time in October 2016. He went on to score twice in 20 appearances for the club.
Durojaiye joined Braintree Town for the 2017–18 season.[11] On 10 September 2018, it was announced that Durojaiye had left the club despite starting all seven league fixtures.[12]
On 21 September 2018, following his departure from Braintree, Durojaiye agreed to join fellow National League side, Maidstone United.[13]
On 26 February 2019, Olumide agreed to join National League South side Woking, following a spell back at Haringey Borough.[14]
Despite gaining promotion during his spell with Woking, prior to the 2019–20 campaign, Durojaiye opted to return to Haringey Borough once more.
On 22 January 2021, Durojaiye rejoined National League South side Welling United.[15] On 18 March 2022, Welling United announced that Durojaiye was one of five players that had left the club.[16]
On 26 March 2022, Durojaiye joined Dartford. He made his debut for the club on the same day, coming on as a second-half substitute in a 1-0 victory at Princes Park against Hampton & Richmond Borough.[17]
On 6 July 2022, Durojaiye joined Hereford.[18] However, on 3 August 2022 - under a month after signing for Hereford and before the National League North 2022-23 season kicked off - Durojaiye left the club having only appeared in a handful of pre-season friendlies.[19]
On 30 July 2023, Durojaiye signed for National League South club Dover Athletic,[20] however departed just one month later having failed to make an appearance.[21]
International career
Durojaiye is eligible to play for Nigeria and England and has previously expressed his desire to represent Nigeria. He was called up to the Under-20 Development squad.[2]
