Obiora, 28, came face-to-face with Bale and Modric when he made his Champions League debut in the 2010/2011 season under Rafa Benitez at Inter Milan.
He came on as a second half substitute at White Hart Lane for the injured Sulley Muntari in a group stage tie.
Spurs went on to win 2-0 after losing the reverse fixture 4-3 at San Siro with Bale netting a hat-trick.
“Yes, going back to my first Champions League match against Tottenham Hotspur I was fortunate enough to encounter Gareth Bale and Luka Modric in the same game,” Obiora told WFi in an interview.
“It was crazy to play against Luka Modric. He was at his peak, in my opinion, before he went to Real Madrid and he is one of the most difficult opponents I have faced in my career so far.
“Gareth Bale also played really well in that match and gave me a tough time. These two players are certainly the toughest that I have encountered so far in my career.”
Obiora joined Inter Milan in 2010 but left in 2011 after making just four appearances.
Despite his short spell at the Serie A giants, Obiora described it as a wonderful experience for him.
“Yes, looking back on my time at Inter Milan it was a wonderful experience for a young player coming all the way from Africa to play and be involved at a major club like Inter Milan,” he said.
“I enjoyed every single minute of it and every bit of it. I have lots of special memories during my time there but the most special one has to be my first Champions League match against Tottenham Hotspur at White Hart Lane in London that certainly is right up there in terms of highlights in my career so far.”
He listed the likes of Samuel Eto’o, Javier Zanetti, Wesley Sneijder and other top stars at Inter back then as the best players he has played with.
“Well, that is an easy question the best players I have played alongside will be the players I played with at Inter Milan.
“Big players such as Samuel Eto’o, Wesley Sneijder, Javier Zanetti, Esteban Cambiasso, Gabriel Milito and Júlio César.
“It was scary and fantastic at the same time for a young player coming into a dressing room with lots of big names like that. They were the biggest players I played with and I cherish my memories of playing alongside them.”
On what he learnt under Benitez, who took over from Jose Mourinho after the Portuguese led them to a famous treble in the 2009/2010 campaign, Obiora said: “That is a tough question. I have had lots of good managers over the years and good coaches too, but the manager who I hold very dear to my heart is Rafa Benitez at Inter Milan.
“He was the one who took my from the youth team to the first team of Inter Milan and he taught me many things and gave me lots of good advice in such a short period of time too.
“The things that he taught me are always in my head and I have brought them with me throughout my career.
“Of all the big managers and good coaches I have encountered in my career, he has certainly played a key role in my development.”
On the biggest moment in his football career, the former Flying Eagles and U-23 Eagles star said it was winning the 2013 AFCON under the late Stephen Keshi.
“Yes, It is every player’s dream to represent their national team and although I was capped by Nigeria at youth international level at under 17, under 20 and under 23 level, when I was capped by the first team of Nigeria was an amazing experience and everything that I could have hoped for.
“I have lots of memories and special times. The biggest was winning the African Cup of Nations with my country. That for me is the most memorable highlight of my career so far.”
And on his time with Portuguese club Boavista whom he joined in 2018: “I am really enjoying my time here so far. Boavista is a traditional club with lots of culture and a good history here in Portugal.
“They have a big fan base too. It is a pleasure to be part of a club with such a good history.
“One of the biggest qualities with have as a team is the never say die attitude we never give up. It does not matter if we are losing or how badly the game is going we never give up. We always keep fighting together as a team.”
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