After gaining momentum in Scotland, Galloway began wrestling dates across the Republic of Ireland with Irish Whip Wrestling (IWW) continuing to use "Thee" Drew Galloway as his gimmick. With Charles Boddington still in his corner, he competed in three contests during his first appearance on 23 July 2005 for "Whiplash TV". After losing to "SOS" Sheamus O'Shaunessy he found a similar fate against Mad Man Manson, sparking a feud between the two. Despite these two losses, his status abroad meant he was already booked in a Ten-Man Gauntlet match to determine the top contender for the main title. Galloway was whitewashed the entire evening, losing to Vic Viper. The following day at "Gym Wars" Manson was absent so Galloway tried to avenge his loss with O'Shaunessy but it ended in a double count-out. Over the next few months Galloway recruited various wrestlers, even his manager Boddington, in a series of tag team and even handicap tag team matches against Manson and his teams. He picked up his first victory in October against Sean South in a warm-up for that event's main event six-man tag team match. The rivalry between Galloway and Manson was finally settled in November at IWW's final show from the SFX Theatre. Their brutal and bloody Street Fight saw Galloway gain respect from for his tenacity and endurance but his losing streak continued.