2019-20 Season (Sophomore) - Flanagan rode plenty for the Bobcats during his sophomore season in 2019-20...Flanagan competed in mountain bike, cyclocross and road racing on the season...Flanagan ended up winning STXC events on back-to-back weekends...First at Lees-McRae's home event at the High Country Collegiate MTB Challenge and then at Lindsey Wilson College in late September...He also took the top spot in the event at Appalachian State's Mountain Bike weekend event in early October...At the USA Cycling Collegiate Mountain Bike Nationals, Flanagan placed 33rd in XC and 25th in STXC...Finished second in his first cyclocross ride of the season in mid-November...Flanagan had plenty of success in the road season as he finished in the top five in each of the five events he rode in in the final criterium standings. 

2018-19 Season (Freshman) - Flanagan particiapted in three cyclocross races during his freshman season...Finished 12th in the A race at King University (Tenn. (Nov. 10)...Posted an eighth-place finish at the SECCC Championships at Warren Wilson (Dec. 1)...Finished 29th in the men's race and was also part of a sixth-place relay team at Collegiate Cyclocross Nationals (Dec. 13-15)...Flanagan also participated in six road races as a freshman...Finished ninth in the A road race, while also finshing 34th in the A criterium event at Auburn (Feb. 23-24)...Finished eighth in the A road race, was part of a fourth-place effort in the team time trial and also finished eighth in the A criterium event at Clemson (Mar. 23-24)...Took third in the day one A criterium, while also winning the day two A criterium at King University (Tenn.) (Mar. 30-31)...Was part of a conference championship team time trial effort, won the A road race for a conference championship and also finished 18th in the A criterium at the SECCC Road Championships (Apr. 6-7)...Finished fourth in the A road race, while finishing third in the A criterium event at the High Country Cycling Classic (Apr. 27-28)...Was part of a fourth-place team time trial effort, finished 11th in the road race and also finished 10th in the criterium event at Collegiate Road Nationals (May 10-12)...Was named to the Conference Carolinas Presidential Honor Roll for his work in the classroom.