Stadium: Estrela Criativa Round: 44 Ground: Hardcourt outdoor
| ITF M15 Sao Bras Alportel | 2019/09/01 11:00 | Rhys Searant v Alan Gleeson | 4-6,6-3,11-9 |
| ITF M25 Dublin | 2019/07/31 15:00 | Matija Pecotic v Alan Gleeson | 6-4,6-1 |
| ITF M25 Dublin | 2019/07/30 12:45 | Philip Lynch v Alan Gleeson | 3-6,3-6 |
| ITF M15 Setubal | 2019/06/25 10:00 | Alan Gleeson v Goncalo Falcao | 6-3,7-5 |
| ITF M15 Setubal | 2019/06/24 12:00 | Pedro Gabriel Rodrigues v Alan Gleeson | 3-6,4-6 |
| ITF Portugal F2 Qual | 2018/02/27 12:50 | Alan Gleeson v Jorge Hernando-Ruano | 6-0,2-6,2-6 |
| ITF Portugal F2 Qual | 2018/02/25 10:00 | Bart Van Den Berg v Alan Gleeson | 3-6,4-6 |
| ITF Portugal F2 Qual | 2018/02/24 12:30 | Juan Jose Lopez Gomez v Alan Gleeson | 4-6,2-6 |
| ITF M25 Tavira | 2019/09/29 13:00 | Matthew Hingley v Ying Hou | 3-6,1-6 |
| ITF M25 Shrewsbury | 2019/09/23 10:00 | Adam Jones v Ying Hou | 6-2,6-2 |
| ITF M15 Tabarka | 2019/09/08 11:30 | Ying Hou v Bjorn Nareyka | 4-6,2-6 |