| — |  | Duccio di BuoninsegnaSiena, around 1300. The child is a small adult and everyone involved agreed to it | — win | — match wins |
| — |  | BerlinghieroLucca, 1230s. Gold ground, long nose, thousand year stare | — win | — match wins |
| — |  | Cimabue at CastelfiorentinoAround 1285. The baby is blessing you whether you asked or not | — win | — match wins |
| — |  | Giotto's laughing childAssisi. A rare medieval baby caught mid laugh, which is arguably worse | — win | — match wins |
| — |  | Barnaba da ModenaNow in the Louvre. Grown man proportions, shrunk to fit the arm | — win | — match wins |
| — |  | Vitale da BolognaThe Madonna of the Teeth. The name is about the child's smile | — win | — match wins |
| — |  | Dietisalvi di SpemeSiena, 1262. Painted before anyone had looked closely at a baby | — win | — match wins |
| — |  | Guido da SienaEnthroned, robed, and staring like a landlord | — win | — match wins |
| — |  | Virgin of the PassionA Greek icon where the child looks like he already knows how this ends | — win | — match wins |
| — |  | Paolo VenezianoVenice, mid 1300s. The face of a man who has read the contract | — win | — match wins |
| — |  | Lippo MemmiSiena. Baby fingers, middle aged forehead | — win | — match wins |
| — |  | Ambrogio Lorenzetti1337, now in the Louvre. He is being held, but he is not a child | — win | — match wins |
| — |  | Master of the Johnson AssumptionThree generations in one panel and the youngest looks oldest | — win | — match wins |
| — |  | Romanesque enthroned MadonnaCarved in wood. Both faces went straight past human | — win | — match wins |
| — |  | Enthroned Virgin and ChildA wooden pair whose expressions have not changed in eight hundred years | — win | — match wins |
| — |  | Duccio's Rucellai MadonnaA detail of the most famous panel in Siena, and the baby is still like that | — win | — match wins |
| — |  | Ugolino di NerioClose up. There is no angle from which this reads as an infant | — win | — match wins |
| — |  | Pietro LorenzettiBuonconvento. Held like a baby, built like a bank manager | — win | — match wins |
| — |  | Simone MartiniAround 1326. Even Siena's smoothest painter could not fix the proportions | — win | — match wins |
| — |  | Segna di Bonaventura1325 or so. The child has been told something disappointing | — win | — match wins |
| — |  | Bernardo DaddiFlorence. Chubby cheeks attached to a fully formed adult skull | — win | — match wins |
| — |  | Taddeo GaddiAround 1355. Giotto's pupil, same baby problem | — win | — match wins |
| — |  | Sano di PietroFifteenth century Siena. The hairline arrived early | — win | — match wins |
| — |  | Giovanni del Biondo1392. Enthroned, and looking at you like you interrupted something | — win | — match wins |
| — |  | Allegretto NuziMadonna of Humility, 1365. The child is not humble | — win | — match wins |
| — |  | Deodato OrlandiLucca, around 1300. Painted with the confidence of a man who never met a baby | — win | — match wins |
| — |  | Lo ScheggiaFlanked by two saints, upstaged by one very serious infant | — win | — match wins |
| — |  | Follower of MelioreFlorence, around 1275. Tempera on canvas, terror on face | — win | — match wins |
| — |  | Lorenzo VenezianoThe Louvre panel. Small body, enormous opinions | — win | — match wins |
| — |  | Michele GiambonoVenice. The child appears to be doing his own taxes | — win | — match wins |
| — |  | Theophanes the CretanByzantine tradition, where the child was always a tiny philosopher | — win | — match wins |
| — |  | Cretan School GlykofilousaThe Virgin of Tenderness, holding something that is not tender | — win | — match wins |
| — |  | Ioannis TzenA Cretan icon with a child who has clearly been briefed | — win | — match wins |
| — |  | The Mother of God GruzinskayaRussian icon. The child has the face of a retired colonel | — win | — match wins |
| — |  | Presbyter MartinusSeat of Wisdom, carved in wood. Wisdom achieved, babyhood skipped | — win | — match wins |
| — |  | Sedes Sapientiae of LiègeThe Virgin as a throne, the child as a very small senator | — win | — match wins |
| — |  | Madonna from OłobokMedieval Poland. Both faces are unreadable in exactly the same way | — win | — match wins |
| — |  | Maria with the Christ ChildCarved oak. The child was given the face of the man who carved him | — win | — match wins |
| — |  | Andrea di BartoloDetroit Institute of Arts. Held tight, entirely unbothered | — win | — match wins |
| — |  | Grifo di TancrediAround 1300, from San Gaggio in Florence. Enthroned and unamused | — win | — match wins |