Prior to joining Clermont Foot, where Sylla signed his first professional contract, he had a year's stint with Ligue 1 club Stade Malherbe Caen. Before that, Sylla had started his career with hometown Parisian club Étampes FC, before joining nearby club CSF Brétigny, which produced France internationalsPatrice Evra and Jimmy Briand. After four years in Brétigny, Sylla spent the next four years roaming around clubs in the Lower Normandyregion such as AS Montferrand, SC Malesherbes, and Caen. And then in 2009, he signed an amateur contract with Clermont where he was inserted into Clermont's reserve team for the 2009–10 season. He appeared in 17 matches scoring one goal.
Clermont
For the 2010–11 season, Sylla was promoted to the senior team by manager Michel Der Zakarian. He made his professional debut on 15 October 2010 in a league match against Le Mans playing the entire match in a 2–0 defeat. Sylla subsequently appeared as a starter in the team's next seven matches. His performances domestically led to interest from German club VfB Stuttgart and Italian club Udinese. In order to decrease the interest Clermont signed Sylla to his first professional contract, which ran from 22 November 2010 until June 2014.
On 31 January 2013, Aston Villa completed the signing of Sylla on a three-and-a-half-year deal, subject to international clearance, after passing a medical.
On 30 August 2017, Panathinaikos officially announced the signing of Malian international defensive midfielder Yacouba Sylla. He joined the Greens on loan from Rennes until the end of 2017–18 season and was the 10th summer signing of the Athens club.
KV Mechelen
On 17 January 2018, Sylla signed a contract with YR KV Mechelen until 2021. He leaves Rennes after having been on loan at Panathinaikos since the end of August.
Strømsgodset
On 1 March 2019, Sylla signed a contract until the end of the 2020 season with Norwegian club Strømsgodset Toppfotball. On 19 May, Sylla scored his first and only goal for the Norwegians, in a 3–1 win against Tromsø IL.
CFR Cluj
On 1 July, he signed a three-year contract with CFR Cluj, Romanian champions.
International career
France
Sylla was born in France but has Malian heritage, which meant that he was eligible to represent either France or Mali. He made one appearance for France's under-21 team on 24 March 2011, in a 3–2 friendly victory over Spain. Sylla was a late substitute for Antoine Griezmann and played the final few minutes of the game.