The 21-year-old beat Sven Ulreich from 30 yards to level things up on Saturday, as Leverkusen went on to beat the champions 3-1 in one of the shocks of the weekend.
“I tricked Sven,” he told Bild after the game – and he was right.
"Bailey often hits it over the wall, that's something we analysed and looked at a lot during the week," Ulreich said.
"I'd already scored a free-kick against him in the other corner [last season],” Bailey explained. “I knew that he often takes a small step towards the side covered by the wall, so I deliberately chose the other side. I caught the free-kick perfectly, it was a good trick."
It was a timely reminder of his ability during what has been a difficult season, the winger struggling for form after being one of the hottest properties on the continent last term.
Bailey’s nine goals and six assists last year attracted the interest of Europe’s elite, prompting the reported interest of Arsenal, Chelsea and Manchester United – as well as a £100 million price tag.
Now, with just two scored and one created in 19 games this year, many are questioning whether the hype was simply superficial.
But Bailey has faced different challenges this year, being rotated in and out of the team in order to ensure a successful Europa League campaign.
This time last year, Leverkusen did not have continental football to juggle and were flying as high as second place. In the end, they would miss out on a Champions League place by only goal difference.
Things aren’t so rosy this time around. Leverkusen may have secured a place in the last 32 of the Europa League, but, domestically, they have been less potent in every attacking area – goals, shots and presence in the opposition’s box - and find themselves in seventh place.
It’s by no coincidence that Bailey has been a more prominent figure in the former competition, rather than the Bundesliga.
That, however, is not necessarily a bad thing. As well as having the first European knockout games of his career to look forward to, the Jamaican is gaining experience of juggling domestic and continental football – in a much more competitive sense than he endured at Genk.
Rumours suggested that Bailey was pondering a January exit for more playing time, but this is a player who knows he is in the perfect place to develop.
Despite being just 21 years old, he has always had a wise head on his shoulders. At 14, Bailey arrived in Europe in search of football, eventually joining FC Liefering in Austria and, later, AS Trencin.
“During our visit in Trencin we could see the club, its way of working and interesting results of developing young footballers. We believe we can continue in our development in Slovakia," Bailey told the Slovakian club's website. It’s a theme that has coloured his words throughout his journey so far.
When he joined Genk two years later, aged 17, he clearly knew the importance of being in a comfortable environment.
“Genk feels like home,” he said. “When I was away at other clubs, I didn't have the support that I had at Genk. Hopefully I can become one of the best players they’ve ever produced.”
He has some competition in securing that crown - with the likes of Kevin de Bruyne, Thibaut Courtois and Kalidou Koulibaly having graced the Belgian club. But he is taking the right steps with Leverkusen - in his own words, "the next important step".
"Leverkusen is well known for its development and the way football is played here is attractive. I like that," he said upon arriving in Germany.
And when the Premier League’s big boys came in for him, he didn’t think twice, telling FourFourTwo: “Manchester United, City, Chelsea, Liverpool – a lot of clubs were interested, but the most important thing as a pro is taking things a step at a time and not rushing to the top too quickly.”
Bailey’s focus is on steadily rising to the top and being the greatest player of his generation. He's made no secret of that ambition, something which has led to conflict with his home nation, as he has not committed to representing Jamaica as a result.
The president of the Jamaican FA, Michael Ricketts, claims that the player has "a slight attitude problem". But many of the game's greats - such as Northern Ireland's George Best and Liberia's George Weah - have learned the hard way that being from a smaller nation can limit a player's potential to be the best.
“I have to think about myself developing as a young player,” he told ESPN. “My aim is to become the best player in the world. For me to achieve that, I need to be on the right path and I think, at this moment, choosing Jamaica is not the right path for me.”
Bailey is certainly capable of reaching that level as he possesses the natural, raw qualities - the lightning pace, direct dribbling and creativity to open up a defence - that only a few at his age can dream of.
He is also capable of justifying his £100m price tag, especially because he understands the importance of time.
“I am focused only on Leverkusen. I am happy where I am now and concentrated on developing well,” Bailey told Sky Germany.
“Who knows what will happen in the future?”