Attitude and talent have allowed the Aberdeen midfielder to carve out a successful career as a professional sportsman but by cold analysis he cannot yet call himself a winner. Ask him what his last winner's medal was for and the answer, delivered in a quiet voice and a strong Dublin accent, comes as a surprise: "I haven't got one."
Actually he does, but not as an adult. Playing for Cherry Orchard in the Dublin and District Schoolboys League, Flood reached a cup final when he was 14, half his life ago. "The Orchard" won but Flood wasn't in a state to enjoy the moment after suffering a dislocated kneecap 15 minutes into the game.
"It was a sore one," he says. "I was on the ground and I looked down: my knee was one way and the kneecap was the other. When they straightened it out, it popped back in. The St John Ambulance guys said I'd be back playing after seven days. Hopefully they were sacked after that game.
"They had a look at my knee in the ambulance and asked me to go for a little 10-yard run. Twenty minutes later my knee was huge. I ended up going to the hospital."
Flood didn't play again for three months. The injury was the first bad one of his career but "The Orchard" have a tie-up with Manchester City and their patronage ensured he was treated properly and recovered fully.
He had already agreed to join City before the injury. "Manchester City were brilliant. Their head of recruitment was at the game and said I would be okay and they made sure I would get looked after. I was lucky I went to such a good club. If it wasn't for them I wouldn't be playing football.
"That was my last winner's medal but God knows where it is. I think it will be in my mum's house back home with cobwebs on it. If I got one on Sunday I am sure that would be kept nice and shiny every day."
By Sunday, Flood is, of course, referring to the League Cup final against Inverness Caledonian Thistle at Celtic Park, a match in which Aberdeen will again rely on this little Irishman - just 5ft 6ins tall and with not a pick of meat on his bones - to be a cornerstone of their side.
A wee metronome in the middle of the park, breaking up opposition moves, winning tackles, shuttling the ball forward, keeping things ticking over, Flood has been a consistently gritty and committed battler in the centre. He's had good games and bad, but his attitude has been consistent. The medal count is deceptive: Flood acts and plays like a winner. "There are better players than Willo Flood who haven't won anything," he says. "Our family will be over for the final so to win would mean a lot. There are a few coming over. My little fella will be going, my missus and family and friends. Half of Dublin will be over with all of Jonny's [Hayes] lot as well. I'm sure a few of Jonny's horses might be over too . . . "
Flood played a few games for City without ever really breaking through. Permanent or loan spells followed with Rochdale, Coventry City, Cardiff City, Dundee United, Celtic, Middlesbrough and Dundee United again. There were some raised eyebrows when he elected to leave the latter for Aberdeen last summer but the effect of one individual on him had been magnetic. When the club approached him last May why had he felt like Aberdeen would shake off years of mediocrity?
"Derek McInnes," Flood replies. "People say, 'you signed for Aberdeen Football Club'. I signed for Derek McInnes first and foremost, and then I signed for Aberdeen Football Club. When I met him I just felt I could work with him and he would get the best out of me. Fingers crossed, it has worked so far. I met him in my house. I spoke to him on the phone and then when he came to see me I said to my missus: 'he will do something'. I made my mind up.
"I previously felt like that with Craig Levein and Gordon Strachan. They were two managers I just got a feel for. Instinct tells you they are the right ones for you. Thankfully for me it has worked out so far. I met Derek and he just gives you confidence straight away when you speak to him.
"He has brought that to the whole club, not just the playing staff. The other people around the club have big smiles on their faces too. He has a good way about him and it is basically because of him that we are where we are. He never looks too far ahead; he just thinks about the next game. When we beat St Johnstone [in the League Cup semi-final], he just wanted us to put that to bed and focus on the league. When we beat Celtic at Celtic Park [in the Scottish Cup] he said to just put a lid on it and focus on the next one. Thankfully that has seemed to work for us so far."
Despite some speculation that his form might earn him a first call-up for the Republic of Ireland - Martin O'Neill's assistant, Roy Keane, watched Flood's outstanding display against Celtic in the cup - there has been no follow-up. "I think that story was growing arms and legs every second day," he says. "I have had no contact and it is not something I have been bothered about. I have never been in the international scene. If it happens, great but if it doesn't, it makes no difference."
Along with Barry Robson, Flood controlled the midfield against Scott Brown and Stefan Johansen that day. Aberdeen won 2-1. Despite having been a Celtic player for a year it immediately became Flood's happiest Parkhead memory. But that, and that Cherry Orchard cup final, could be supplanted on Sunday.