Tottenham v Bayern Munich: Timing is everything in Philippe Coutinho's pursuit of Champions League glory

In Munich, they already speak with awe about the precision timing of Philippe Coutinho. Robert Lewandowski, the prolific Bayern centre-forward, felt so grateful for all the perfectly calibrated passes coming his way he even let Coutinho take over penalty-taking duties for a day. At the weekend, Serge Gnabry thanked his new teammate for the latest assist with a payback of a cross, to give the Brazilian a tap-in for his second goal in as many games. Coutinho's clockwork delivery is among the finest of his many assets. The timing of some of his career decisions has been much less astute. Bayern, whom he joined on loan at the tail-end of the transfer window, are the third major club he has played for in the last 20 months in his pursuit of major honours and a sense of belonging. On Tuesday night, a reminder of that restlessness: a year on exactly since he dazzled Tottenham Hotspur in the Uefa Champions League in a Barcelona jersey, he is there again, in another shirt, hoping that, at last, he might have made the right choice. As it happens, Spurs were eager to take on Coutinho, when, with his first-team place at Barcelona far from guaranteed, he was made available by the Catalan club in August. Mauricio Pochettino, the Tottenham manager, knows him well from when a 19-year-old Coutinho played at Espanyol, where Pochettino was building his coaching career. That too was a loan, a successful one, the boyish Brazilian lent out by Inter Milan to gain experience. He had been 16 when Inter signed him up, 18 when he was permitted to first play for them, a prodigy feted as "our future" by the club’s then president Massimo Moratti. He made his debut in the European Super Cup, which Inter contested because of their triumph in the 2010 Champions League final. That was the first hint of what would turn into Coutinho’s long, teasing relationship with the most prestigious club competition, the saga where he keeps missing out on European Cup finals, never at the right club at the right time. Liverpool signed Coutinho from Inter in the winter of 2013, a shrewd move, at an absolute snip: the fee, around €10 million (Dh40.1m), was not much greater than just the loan payment Bayern have made to Barcelona to have him for nine months. He reached a Europa League final. But the big prizes, he felt, were always tantalisingly at arm’s length. Coutinho, the hard-working artist with the benevolent face and no flashy trappings of stardom, was loved at Anfield, although the affection diminished once he started engineering an exit, convinced the only way to win trophies was to go elsewhere. He got his way in January last year, Barcelona agreeing to a mammoth initial fee of around €115m, with additional clauses that would potentially lift it above €150m. That price burdened the player with vast expectation. So did the timing: Coutinho of Camp Nou was required to replace both Neymar and give evidence he could become Barca’s new Andres Iniesta. Home fans booed Coutinho when he was neither. Liverpool, investing the money from his transfer wisely, promptly reached the Champions League final four months after he left, Barcelona eliminated in the quarters. At times last season, he seemed to have turned a corner, especially the night at Wembley when he scored after two minutes, and set up another in a 4-2 win over Pochettino’s Spurs. But the European adventure ended with Coutinho once again on the wrong train. Spurs reached the final; Liverpool knocked out Barcelona and their chastened former darling in an extraordinary semi and they went to lift the prize Coutinho has so ardently pursued. Inter, Liverpool, Barcelona, Bayern. Between them, those clubs have won five of the last 10 European Cups. Coutinho, nine years in European football, has now played for each. It's a handsome portfolio of employers and different leagues, but it also traces a hopscotch journey that has bypassed the historic nights. Bayern wonder, though, if they have found just the player to bridge their frustrating Champions League gap, to break a habit that has left them losing semi-finalists four times in the last six years. He looks at home. A month into his Bundesliga career, the Allianz Arena already knows to rise to its feet at the distinctive Coutinho dart, the neat step on to his right foot as he swoops through the inside left channel, like a looking-glass version of Arjen Robben. “He looks like he’s dancing with the ball,” said Bayern manager Niko Kovac after Coutinho had contributed crucially to Saturday’s 3-2 win at Paderborn. “And all the time he knows exactly where, how and when he’s going to release it.” A few more weeks like that and Bayern, who have an option to buy the Brazilian from Barcelona for €120m, will wonder how, when, or if they can possibly release him.

Tottenham v Bayern Munich: Timing is everything in Philippe Coutinho's pursuit of Champions League glory

Brazilian playmaker has spent much of his career at European Cup-winning clubs without ever landing the prize himself