Ogilvie started his career in Tottenham Hotspur's academy since July 2012.[3] After progressing throughout the ranks of the academy and the development squad,[3] Ogilvie was included in the squad for the first team in the UEFA Europa League match as unused substitute in a 2–2 draw against Benfica on 20 March 2014.[4]
Whilst on loan, Ogilvie signed a two-year contract with the club, keeping him until 2017.[5] Then ahead of the 2017–18 season, Ogilvie signed a two-year contract with the club.[6]
Loan spells
On 14 August 2015, Ogilvie joined League Two club Stevenage on a one-month loan.[7] He made his debut in a 2–0 win against Hartlepool United on 22 August 2015,[8] and scored his first professional goal in a 2–1 win against Plymouth Argyle on 5 September 2015,[8] then assisted a goal against York City in a 2–2 draw in his next match.[9] His loan was extended until January after his impressive performances.[10] On 14 November, his free kick assisted a late equaliser against Yeovil Town.[11] Later, his loan was extended every month until the end of the season.[12] Despite being sidelined out of the first team on four occasions.[13][14][15][16]
On 24 January 2017, Ogilvie was loaned back to Stevenage until the end of the season.[17] Ogilvie's first appearance back at Stevenage in his second loan spell came on 28 January 2017, in a 2–0 win over Grimsby Town.[18] Since re-joining Stevenage, Ogilvie re-established himself in the first team, making 18 appearances for the side.[19]
On 7 July 2017, Ogilvie signed a new two-year contract and was loaned to League One club Gillingham until January 2018.[20] He made his Gillingham debut in the opening game of the season, in a 0–0 draw against Doncaster Rovers.[21] Initially playing in the left-midfield position, he played in the left-back position.[22] Gillingham re-signed Ogilvie on loan for the first half of 2018–19 season, later extending this until the end of the season.[23]
Gillingham
After two loan spells at the club Ogilvie joined Gillingham on a permanent deal in May 2019 signing a two-year contract.[24][25] He was named as the Kent side's Player of the Season at the conclusion of the 2019–20 season.[26] Ogilvie rejected the offer of a new contract by the club at the end of the 2020–21 season.[27]
Portsmouth
On 2 August 2021, Ogilvie joined Gillingham's League One rivals Portsmouth on a free transfer, signing a two-year contract with the potential for a third.[28] He scored his first goal for the club on 11 December 2021 in a 2–0 win against Morecambe.[29]