Liverpool face an uphill task to qualify for the latter stages of the Champions League after falling to defeat at Besiktas.
Gerrard gave Liverpool hope but was quiet for much of the game
The hosts were gifted their first when Sami Hyypia deflected in Serdar Ozkan's strike and they doubled their lead when Bobo slid the ball under Pepe Reina.
Steven Gerrard gave Liverpool hope with a flying header on 85 minutes but it was too late for Rafa Benitez's side.
The Reds are now bottom of Group A with one point from three matches.
Liverpool were put on the backfoot straight away by Besiktas, whose defender Serdar Kurtulus went close with a 25-yard effort that flew just two yards over Reina's bar.
The Reds looked like a team under pressure and it took until the second half for their reorganised midfield to show any sort of cohesiveness.
Their defence also looked nervy with the ball over the top and down the wings, and a mix-up in their own penalty area led to the Besiktas opener.
Bobo was a little terror during the match and his pull-back from the byeline, after chasing a hopeful ball, fell to the feet of Ozkan whose snap-shot from eight yards deflected off Hyypia's leg and past Reina.
In these situations the Reds would look to Gerrard, but the skipper was both looking out-of-sorts and was being well marshalled by a disciplined Besiktas side.
When he was allowed to escape he was a threat and the England international came close to giving them the equaliser, but his poke, following a classy one-two with Dirk Kuyt, brought out a good reaction save from Hakan Arikan.
Serdar Ozkan celebrates his goal
Kuyt's strike partner Andriy Voronin messed up Liverpool's best chance of the first half when he failed to connect with a ball from three yards out after defender Gokhan Zan's tame clearing header.
The Premier League side pressed after the break but opportunities were few, and when one came their way, it fell to Hyypia who mistimed his volley from 10 yards.
They were made to pay for their lack of spark when the impressive Bobo was sent clear by Uzulmez before composing himself and passing his shot under the body of the on-rushing Reina.
Liverpool unleashed more men forward and finally got some reward when Gerrard chanced his arm - well, his head - and gave his side a lifeline in spectacular style.
The last few moments were desperate for Besiktas and Liverpool but the home side held out.
Besiktas: Arikan, Tandogan, Zan, Toraman, Uzulmez, Kurtulus (Avci 42), Cisse, Tello, Ozcan, Bobo (Diatta 86), Delgado (Higuain 62).
Subs Not Used: Ozmen, Yozgatli, Nobre, Ricardinho.
Goals: Hyypia 13 og, Bobo 82.
Liverpool: Reina, Finnan, Carragher, Hyypia (Crouch 83), Riise, Pennant (Benayoun 59), Gerrard, Mascherano (Lucas 76), Babel, Voronin, Kuyt.
Subs Not Used: Itandje, Alonso, Sissoko, Hobbs.
Goals: Gerrard 85.
Ref: Claus Bo Larsen (Denmark).