Gastric outflow obstruction (GFO) occasionally requires surgical intervention in foals when medical management fails. Current literature lacks consensus on several surgical decisions, with most comprehensive reports dating back over a decade. Critical aspects—including jejunal loop orientation and necessity of jejunojejunostomy—remain debated among surgeons. Long-term data regarding complications, growth, and athletic performance are scarce. This case series documents the long-term outcomes of two Lusitano dressage foals that underwent bypass surgery for GFO, providing contemporary outcome data for specific surgical decisions where evidence remains limited. Two Lusitano foals underwent bypass procedures for GFO. Case 1: A 15-day-old orphan foal with pyloric stenosis underwent side-to-side gastrojejunostomy without jejunojejunostomy, with jejunal loop oriented left-to-right. Six years post-operatively, the horse performs dressage at a competitive level with normal growth and conformation. Case 2: A 12-hour-old foal underwent gastroduodenostomy; nearly three years later, it continues without complications. This series contributes recent outcome data for specific surgical decisions in bypass procedures. Both foals achieved favourable results. Left-to-right orientation gastrojejunostomy and without jejunojejunostomy worked perfectly. Importantly, extended follow-up documents the absence of long-term complications, normal growth, and athletic performance—critically needed information for surgical decision-making and owner communication regarding these uncommon, costly procedures.