Flora Ojamaa began playing football with the
Flora youth academy. He made his senior league debut for the club's reserve side
Flora II in the
Esiliiga on 4 April 2007.
Derby County In 2007, Ojamaa joined the
Derby County academy. He was Derby County's Scholar of the Year in the 2008–09 season. In June 2009, he signed his first professional contract. On 28 November 2009, Ojamaa joined
Stafford Rangers on a one-month loan. He won numerous Man of the Match awards during his short spell at the
Conference North side. On 5 May 2010, it was announced that Ojamaa would be released after the
2009–10 season.
Alemannia Aachen On 19 May 2010, Ojamaa signed a two-year contract with
2. Bundesliga club
Alemannia Aachen. He made a single appearance in the 2. Bundesliga on 27 November 2010, replacing
Babacar Gueye in the 88th minute of a 1–3 loss to
FC Augsburg at
New Tivoli.
Fortuna Sittard (loan) In January 2011, Ojamaa joined
Eerste Divisie club
Fortuna Sittard on loan for the remainder of the
2010–11 season.
RoPS On 22 July 2011, Ojamaa signed for the
Veikkausliiga club
RoPS for the remainder of the
2011 season. He went on to score two goals in 17 appearances, but couldn't save his club from relegation.
Motherwell On 4 January 2012, Ojamaa signed for
Scottish Premier League club
Motherwell until the end of the
2011–12 season. He made an instant impact on his debut for Motherwell, scoring in a 4–0 home win over
Queen's Park in the fourth round of the
Scottish Cup on 7 January 2012. Ojamaa made his debut in the Scottish Premier League on 14 January 2012, when he came on as a 71st-minute substitute for
Omar Daley in a 0–1 home loss to
Inverness Caledonian Thistle. He scored four goals in his first five appearances for Motherwell and on 2 February 2012, he signed a new two-and-a-half-year contract with the club. Ojamaa celebrated his contract extension with another goal and two assists in a 6–0 victory over
Greenock Morton in a Scottish Cup match on 4 February 2012. Ojamaa became referred to as "The Sheriff" by fans during his stay at Motherwell due to his pistols goal celebration. His performances in January 2012 led to him being named Scottish Premier League
Young Player of the Month, as well as the player of the fifth round of the Scottish Cup. In addition to his four goals in the
2012–13 season, Ojamaa was also the league's top assist provider with 16.
Legia Warsaw On 6 June 2013, Ojamaa signed a three-year contract with Polish champions
Legia Warsaw for a fee of €500,000. He made his debut in the
Ekstraklasa on 27 July 2013, coming on as a substitute and providing an assist for
Vladimir Dvalishvili's goal in the 3–0 away victory over
Pogoń Szczecin. Ojamaa scored his first Ekstraklasa goal on 3 August 2013, in a 4–0 home victory over
Podbeskidzie Bielsko-Biała. He won the Ekstraklasa title in the
2013–14 season, his first league title.
Motherwell (loan) On 14 August 2014, Ojamaa returned to Motherwell on a six-month loan deal. At the conclusion of the loan in January 2015, Ojamaa opted not to extend his stay at Motherwell and returned to Legia Warsaw.
Sarpsborg 08 (loan) On 2 February 2015, Ojamaa joined
Tippeligaen club
Sarpsborg 08 on loan. He made his debut in the Tippeligaen on 6 April 2015, in a 1–0 away victory over
Tromsø.
Swindon Town On 4 September 2015, Ojamaa signed for
League One side
Swindon Town on a one-year deal. He made his debut for Swindon Town on 12 September 2015, in a 1–4 away loss to
Barnsley.
Wacker Innsbruck On 7 January 2016, Ojamaa signed for
Erste Liga club
Wacker Innsbruck.
Go Ahead Eagles On 21 June 2016, Ojamaa signed a two-year contract with
Eredivisie club
Go Ahead Eagles. He made his debut in the Eredivisie on 6 August 2016, starting in a 0–3 away loss to
ADO Den Haag. Ojamaa scored in his second match, a 2–2 home draw against
NAC Breda on 14 August 2016.
Dundee (loan) On 31 January 2017, Ojamaa joined Scottish Premiership club
Dundee on loan until the end of the
2016–17 season.
Gorica On 21 October 2017, Ojamaa signed for
Druga HNL club
Gorica until the end of the
2017–18 season. He scored 6 goals in 19 games as Gorica won the league and promotion to the
Prva HNL.
Miedź Legnica On 21 June 2018, Ojamaa signed for Ekstraklasa club
Miedź Legnica on a two-year deal, with an option to extend the contract for another year. ==International career==