He joins the region from Cardiff Blues, where he has made 25 appearances (10 starts) since his debut against Munster at the tail-end of the 2005/06 season, scoring 41 points. Hailing from Cefn Hengoed in the Rhymney Valley, Flanagan first came to attention as a 17-year old at Pontypridd, and is best known for his injury time drop goal to win the 2006 Konica Minolta Cup Final at the Millennium Stadium for Ponty against Neath. Standing 1.83m tall and weighing 86kg, Flanagan has been capped by Wales at U16, U19 and U21 level.
Speaking after signing his contract, Flanagan said: "I'm delighted to have signed for the Ospreys and I'm really looking forward to the challenges ahead of me. There's real competition for places in the squad which is a good thing, I realise there are some excellent fly-half at the region, but I'm coming to the Ospreys to prove myself.
"I've been with the Blues since 2004 so it's going to be a bit strange, it's a big change for me, but it's a challenge I'm looking forward to. I wouldn't have signed if I thought that I'm just be going to make up the numbers and wouldn't get any game time. It's a long season, and with the international commitments that the Ospreys have then there's plenty of opportunities for me to show what I can do. I believe in myself and the ability I have, but I really feel that with the set-up there then I can progress as a player over the next few years. "
Ospreys Director of Coaching, Scott Johnson, commented, "Dai is a talented young Welsh kid who was looking for a fresh opportunity, so we're pleased to have him here and to be able to give him that chance. He fits the bill for us in that we are trying to be a bit more predictive with our recruitment at the moment, as to who is going to be missing for international reasons for long periods of the year.
"He plays in a position where we think we are likely to lose a number of Wales players regularly. We've already got Dan Biggar and James Hook involved with the Welsh squad, and we can see Gareth Owen joining them in the very near future, so this is a sensible signing that will provide an extra option where it is needed. He's done a pretty good job whenever he's played so we're keen to have him here and to help him kick-on with his career
"With the restrictions placed on us in terms of signing non-Welsh players, it is an ideal opportunity for us to give him a go. I've worked with the kid before when I was with Wales and he was coming through the system alongside Hooky. I know his background, his attitude and his ability, so I have every reason to believe he will prove to be a success as an Osprey. We know the impact that national call-ups has on us during the season so in that respect, he's a nice acquisition for an area where we know we will be hit hard at international level, and will help us to compete on all fronts throughout the year."