Milos Raonic beats Aljaz Bedene 6-7 6-3 7-6 at Istanbul Open

Aljaz Bedene suffered defeat at the Istanbul Open, but only after pushing world no 3 and top seed Milos Raonic in a three-set epic.

Despite taking the first set, Bedene went down 6-7 6-3 7-6 against the Canadian who is making his return having been out since withdrawing from the Miami Open in March.

The British number three has been on a roll on his favoured surface, having reached the final in Budapest last week after victories in his previous two Challenger events. But his bid to continue that run in Turkey ended at the second-round stage.

Having lost all 10 previous meetings with top 10 players, Bedene made a solid start against a rusty Raonic, claiming the opening set on a tie-break.

But as Raonic found his range, the big-serving Canadian powered to the second set to level the match before an epic third ensued with Bedene battling back from 4-1 down in the tie-break, only to eventually see Raonic prevail.

Also in Istanbul there were routine victories for second seed Marin Cilic and sixth seed Bernard Tomic who advanced to the quarter-finals.

Tomic, who withdrew in Barcelona last week, followed up a three-set first round win over Mohamed Safwat with a 7-5 6-3 success against Brazil's Rogerio Dutra Silva and he will now face Raonic in the last eight.

Cilic made the most of his wild card into the event by sinking Damir Dzumhur 6-4 7-5 to advance to a quarter-final showdown with Belgium's Steve Darcis who was an impressive 6-2 6-1 winner over Czech Republic's Jiri Vesely.

In Munich, Alexander Zverev remained on course for a final showdown with his older brother Mischa by beating France's Jeremy Chardy

The Zverev brothers are in opposite sides of the draw and Mischa will face Martin Klizan in their second round match on Thursday while Alexander will face another German in the quarter-finals after seventh seed Jan-Lennard Struff was too strong for Tommy Haas.

World no 273 Yannick Hanfmann delighted the home crowd by knocking out eighth seed Thomaz Bellucci - the German qualifier coming through 7-6 4-6 7-5.

He will next face second seed Roberto Bautista Agut who also needed three sets before eventually beating Romania's Marius Copil 4-6 7-6 7-5.

In Portugal at the Estoril Open, top seed Pablo Carreno Busta kept up his campaign with a hard-fought victory over Spanish veteran Tommy Robredo.

The 25-year-old prevailed against Robredo, 10 years his senior, to set up another all-Spanish showdown and repeat of last year's year final against Nicolas Almagro, who dropped just three games against Gastao Elias.